GB1157638A - Aminonitrile Derivatives and Process for their Preparation - Google Patents
Aminonitrile Derivatives and Process for their PreparationInfo
- Publication number
- GB1157638A GB1157638A GB174669A GB174669A GB1157638A GB 1157638 A GB1157638 A GB 1157638A GB 174669 A GB174669 A GB 174669A GB 174669 A GB174669 A GB 174669A GB 1157638 A GB1157638 A GB 1157638A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- preparation
- july
- hydroxy
- stage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000005219 aminonitrile group Chemical group 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- FPPLREPCQJZDAQ-UHFFFAOYSA-N 2-methylpentanedinitrile Chemical compound N#CC(C)CCC#N FPPLREPCQJZDAQ-UHFFFAOYSA-N 0.000 abstract 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- NGCJVMZXRCLPRQ-UHFFFAOYSA-N 2-methylidenepentanedinitrile Chemical compound N#CC(=C)CCC#N NGCJVMZXRCLPRQ-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 238000005932 reductive alkylation reaction Methods 0.000 abstract 1
- 229910000018 strontium carbonate Inorganic materials 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,157,638. Aminonitrile derivatives and their preparation. STERLING DRUG Inc. 1 July, 1966 [1 July, 1965], No. 1746/69. Divided out of 1,157,637. Heading C2C. Compounds of the formulae may be obtained by reductively alkylating 2- methylglutaronitrile in the presence of an amine, HNR 1 R 2 , where NR 1 R 2 is a tertiary amino group and R 1 and R 2 are the same or different and represent lower or higher alkyl, hydroxy lower or higher alkyl, lower alkoxy higher or lower alkyl, di-lower alkylamino lower or higher alkyl, C3<SP>_</SP>7 cycloalkyl, phenyl or substituted phenyl, said substitutents being hydroxy, lower alkoxy, di-lower alkyl amino, trifluoro methyl, lower alkyl mercapto or halo, or R 1 and R 2 taken together form a heterocyclic ring containing at least one heteroatom, the terms " lower and " higher " denoting C 1-8 and C 8-18 respectively. The 2-methyl glutaronitrile may be prepared in a first stage by reducing 2- methylene glutaronitrile at 60-80‹ C. under a pressure of 100-200 p.s.i. hydrogen in the presence of a catalyst such as palladium, platinum, Raney cobalt or Raney nickel which may be supported on a carrier such as carbon, barium sulphate, strontium carbonate, calcium carbonate or alumina. The reductive alkylation step is preferably effected at 90-110‹ C. under a hydrogen pressure of 100-500 p.s.i. employing the same catalyst as in the above first stage. Example 3 also illustrates the preparation of a compound of the Formula I by alkylation of the corresponding free amine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46895865A | 1965-07-01 | 1965-07-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1157638A true GB1157638A (en) | 1969-07-09 |
Family
ID=23861890
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB174669A Expired GB1157638A (en) | 1965-07-01 | 1966-07-01 | Aminonitrile Derivatives and Process for their Preparation |
| GB174769A Expired GB1157639A (en) | 1965-07-01 | 1966-07-01 | Amino-Valeramide Derivatives and Process for their Preparation |
| GB2963666A Expired GB1157637A (en) | 1965-07-01 | 1966-07-01 | Process for the Production of Tertiary-Amino Alkylated Primary Amines |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB174769A Expired GB1157639A (en) | 1965-07-01 | 1966-07-01 | Amino-Valeramide Derivatives and Process for their Preparation |
| GB2963666A Expired GB1157637A (en) | 1965-07-01 | 1966-07-01 | Process for the Production of Tertiary-Amino Alkylated Primary Amines |
Country Status (1)
| Country | Link |
|---|---|
| GB (3) | GB1157638A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0599180A1 (en) * | 1992-11-26 | 1994-06-01 | BASF Aktiengesellschaft | Process for the preparation of diamines |
| US5463130A (en) * | 1994-03-07 | 1995-10-31 | Basf Aktiengesellschaft | Preparation of peralkylated amines |
| US6198002B1 (en) | 1998-06-06 | 2001-03-06 | Basf Aktiengesellschaft | Preparation of secondary and tertiary 2-methyl-1, 5-pentanediamines |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4910343A (en) * | 1988-09-20 | 1990-03-20 | W. R. Grace & Co.-Conn. | Nitroamines |
| CN104803859A (en) * | 2015-04-17 | 2015-07-29 | 武汉瑞凯兴科技有限公司 | Synthetic method of 5-(N-ethyl-N-2-ethylol amine)-2-amylamine |
| CN110616236B (en) * | 2019-10-14 | 2021-02-26 | 暨明医药科技（苏州）有限公司 | Preparation method of (R) -N1, N1-diethyl-1, 4-pentanediamine |
| CN111253263B (en) * | 2020-02-17 | 2022-07-05 | 北京弗莱明科技有限公司 | Preparation method of chloroquine key intermediate 2-amino-5-diethylaminopentane |
-
1966
- 1966-07-01 GB GB174669A patent/GB1157638A/en not_active Expired
- 1966-07-01 GB GB174769A patent/GB1157639A/en not_active Expired
- 1966-07-01 GB GB2963666A patent/GB1157637A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0599180A1 (en) * | 1992-11-26 | 1994-06-01 | BASF Aktiengesellschaft | Process for the preparation of diamines |
| US5557011A (en) * | 1992-11-26 | 1996-09-17 | Basf Aktiengesellschaft | Preparation of diamines |
| US5463130A (en) * | 1994-03-07 | 1995-10-31 | Basf Aktiengesellschaft | Preparation of peralkylated amines |
| US6198002B1 (en) | 1998-06-06 | 2001-03-06 | Basf Aktiengesellschaft | Preparation of secondary and tertiary 2-methyl-1, 5-pentanediamines |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1157639A (en) | 1969-07-09 |
| GB1157637A (en) | 1969-07-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |