ES262485A1 - Dibenz[b,f]azepines and process for their preparation - Google Patents
Dibenz[b,f]azepines and process for their preparationInfo
- Publication number
- ES262485A1 ES262485A1 ES0262485A ES262485A ES262485A1 ES 262485 A1 ES262485 A1 ES 262485A1 ES 0262485 A ES0262485 A ES 0262485A ES 262485 A ES262485 A ES 262485A ES 262485 A1 ES262485 A1 ES 262485A1
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- compound
- azepines
- dibenzo
- alkyl
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000001538 azepines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- -1 dibromo compound Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- OSQPHLCMJMVXLB-UHFFFAOYSA-N 1-(5H-dibenzo[b,f]azepin-5-yl)ethan-1-one Chemical class C1=CC2=CC=CC=C2N(C(=O)C)C2=CC=CC=C21 OSQPHLCMJMVXLB-UHFFFAOYSA-N 0.000 abstract 1
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0943277/C2/1> (wherein X and Y represent hydrogen atoms, symmetrically disposed identical halogen atoms, or symmetrically disposed methyl groups, and R represents an alkyl or alkenyl radical of at most 5 carbon atoms), and the preparation thereof by treating a compound of the general formula: <FORM:0943277/C2/2> (wherein Z represents a C1-5 alkyl or alkoxy radical) with bromine to form a dibromo compound of the general formula: <FORM:0943277/C2/3> and treating this with two molecular proportions of an alkali metal compound of an alcohol ROH to form a compound of the first general formula above, which, if desired, is hydrolysed to a compound of the second general formula, or by a modified process in which the dibromo compound is first treated with an inorganic or organic basic substance to form a monobromo compound of the general formula: <FORM:0943277/C2/4> and this is then treated with at least an equimolecular proportion of the alkali metal alcoholate. The products are useful as intermediates in the synthesis of medicaments. 5-Acetyl-5H-dibenzo[b,f]azepines of the third general formula above (in which Z=CH3) are prepared by acetylation of the corresponding 5H-dibenzo[b,f]azepines, or of their 10,11-dihydro derivatives with subsequent bromination with bromosuccinimide and splitting off of hydrogen bromide under conditions not affecting the acetyl group.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH8063459A CH383977A (en) | 1959-11-16 | 1959-11-16 | Process for the production of new azepine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES262485A1 true ES262485A1 (en) | 1961-06-01 |
Family
ID=4538106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0262485A Expired ES262485A1 (en) | 1959-11-16 | 1960-11-15 | Dibenz[b,f]azepines and process for their preparation |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES262485A1 (en) |
| GB (1) | GB943277A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH605791A5 (en) * | 1974-09-27 | 1978-10-13 | Ciba Geigy Ag | |
| US7982032B2 (en) * | 2004-03-11 | 2011-07-19 | Sun Pharmaceutical Industries Limited | Process for the preparation of 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide |
| CN115650918A (en) * | 2022-11-23 | 2023-01-31 | 浙江华洋药业有限公司 | A preparation process of high-purity and low-impurity 10-methoxyiminostilbene |
-
1960
- 1960-11-15 ES ES0262485A patent/ES262485A1/en not_active Expired
- 1960-11-16 GB GB3927060A patent/GB943277A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB943277A (en) | 1963-12-04 |
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