SU625599A3 - Method of producing amines and their salts - Google Patents

Description

I

A method for producing new amines of the general formula

W,) Kg) AgOSN2CHSNMK-S- (y

2

"Th

where R is in position 2 or 3 group -CHjCH -CHj, -OCHj ,, -OCHj, CaCH,

C. -C-papil, C, -C. alkoxyalkoxyl, "(i. b10

HOCHj CI NHCOCHj O is ,, jCH HCOCH O or a group in which is hydrogen or a kil. from 1-3. carbon atoms |

1 - hydrogen or halogen {

R and R is hydrogen or methyl; jg

R is hydrogen, alkoxycarbonylaminoyl kil with 2-5 carbon atoms in the alkyl and alkoxy groups, cyano group, the group in which R and R are hydrogen or y20

R and R together with the nitrogen atom form a morpholine ring |

U - oxygen or methylene rpynnaj

П - integer О-5j АР - phenyl group, 25

moreover, if Y is SI, then n is 15, if R is methyl, then it is not bound to phenyl in position 2, except for the case when R is alkoxycarbony-amio alkyl, and if R is 3-isobutyl, then {and f don't mean methyl

or their salts, possessing biological activity.

The literature describes various methods for the preparation of amines, including aryloxy amines, for example, by reducing the amides and phenoxylation of the corresponding halo derivatives (ij, however, there is no information about the method for preparing compounds of general formula 1.

The aim of the invention is to expand the range of vesicles with biologic activity and to obtain compounds of general formula 1.

The proposed method for the preparation of amines of general formula 1 is that the compound of general formula

(R.KSj ArOH (2) 6 where Af, F and R have the indicated meanings} M is hydrogen or an alkali metal, is reacted with a compound of the general formula X "3 II 7 - cis snsn-km-c- (cis) I k, "where R P has the indicated meanings; X is hydroxyl; 2. the reactive esterified ester is a hydroxyl group or X and 1, together form an epoxy ™ group, in medium C, -C, alkanol at the boiling point of the reaction medium. Preferably, the compound of the general formula 2 is used in the form of a phenol metal, for example an alkali metal phenol, or else the reaction is carried out in an additive As an acid bonding agent, preferably in the presence of an agent that can form a salt of a compound of the general formula 2, for example, an alkali metal alcoholate. The desired products are isolated from the reaction mixture by known methods in free form or salt form. sodium is dissolved in 10O ml of ethanol and then 18.0 g of 2-allylphenol and 19.0 g of 1-H2 - (4-carbamylphenoxy) ethyl-mino-3-chloropropanol-2 are added. The mixture is heated in an autoclave on a boiling water bath for 15 hours. Then the reaction mixture is filtered and the filtrate is evaporated to dryness. To the residue is added 2N. hydrochloric acid and the solution is extracted with ether. The aqueous phase is alkalinized 2 n. sodium hydroxide and extracted with ether. The ether phase is dissolved over potassium carbonate and then the hydrochloride is precipitated with gaseous hydrogen chloride. This gives 20.4 g (72% of the theoretical). Hydrochloride (4-carba mil of phenic and) ethyl min oj -3- (2-allylphenoxy) propanol-2, so pl. 211 C. Example 2. 1, O g of sodium is dissolved in 10 O ml of methanol and 18.0 g of 2-allylphenol and 19.0 g of -carbamylphenoxy) ethylamino-3-chloropropanol-2 are added. The mixture is heated in an autoclave on a boiling water bath for 15 hours. Then the reaction mixture is filtered and the filtrate is evaporated to dryness. 2N was added to the residue. hydrochloric acid and rastor are extracted with ether. The aqueous phase is alkalinized 2 n. hydroxide extract and extract with ether. The ether phase is dissolved over sodium carbonates and then the hydrochloride is precipitated with gaseous hydrogen chloride. 19.5 g (69% of theory) of 4-carbamide 11-phenoxy-ethyl-amino-3- (2-allyl-phenoxy) propanol-2 hydrochloride are obtained, mp. 211 ° C. Example 3. 5.5 g of potassium are dissolved in 100 ml of isopropanol and 18.0 g of 2-allylphenol and 19.0 g of (4-carbamylphenoxy) ethylamino-2,3-epoxypropane are added. The mixture is heated in an autoclave on a boiling water bath for 2 hours. Then the reaction mixture is filtered and the filtrate is evaporated to dryness. 2N hydrochloric acid is added to the residue and the solution is extracted with ether. The aqueous phase is made alkaline 2.N. sodium hydroxide and extracted with ether. The ether phase is dried over sodium carbonate and then the hydrochloride is precipitated with gaseous hydrogen chloride. 20.1 g (71% of theory) of 1- {2- (4-carbamylphenoxy) ethylamino-3- are obtained. - (2-al / shlphenoxy) propanolag-2, so pl. 211 C. Analogously to examples 1-3, the following compounds are obtained: hydrochloride (4 carbamylphene si) ethylamino-3- (2-chloro-5-methylfbnoxy) propanol-2, yield 68% of theoretical, mp, pl, 25 ° C (decomposition) jf hydrochloride 1-p1-megyl-2- (4-carbamylphenoxy) ethylenamine -3- (2-allylphenoxy) propanol-2,. T, mp, yield 69% of theoretical; 1- 1-metsh1-2- (2-methylphenoxy) ethyl hydrochloride mino-3- (2, -allylphenoxy) propnnola-2, mp, 142 ° C, yield 66% of theoretical; 1-1-methyl-2- (4-methylphenoxy) ethyl mino-3- (2-allylphenoxy) propanol-2 gdrochloride, m.p. 146 ° C, yield 68% of theoretical; 1- G1-methyl-2- (4-carbamoylphenoxy). ethyl (2-methyl zonitrosomethylphenoxy) propanol-2, so pl. 1O6 C (as hydrochloride), yield 62% ogteoretic; (2) -2-methyc icarb oril mino o (et il) fenoc yat silt mino-3- (2-methylphenoxy) propanol-2 (as base), t, mp, 93 ° C, yield 65% of theoretical; (4-carbamal-pheno-x-9) ethylamino-3- (3-aplylphenoxy) propanol-2, mp, 228С (as hydrochloride), yield 71% of the theoretical. Other compounds whose properties are listed in the table are obtained in the same way. 62 -7 F b p m in l of inventions 1. A method for producing amines of the general formula p. ONK, II (k,) (K2) Agosng snsnn-s- “CIS) g where RI is in position 2 or 3 group -CHj (cn4: Hj ,, x: HtCH: Hi, -ocHjCsCH,, Q-Cj- alkoxyalkoxy, HOCHjCH rt (COCHaO-.HjOCHjCH NHCOCH, 0 or a group in which R is hydrogen or alkyl with 1-3 carbon atoms is hydrogen or halogen; Rj and hydrogen or methyl | Rg is hydrogen, alkoxycarbonyl-amino-alkyl with 2-5 atoms carbon in the alkyl and alkoxy groups, the cyano group, the -CWRgR group, and which and RI are water or Rg and R together with the nitrogen atom form a moriline ring; y is oxygen or methylene group | P is an integer O-5 | A g - phenyl group, moreover, if Y is CHj, then Pa 1-5, if R is methyl, then it is not bound to phenyl in position 2, except when Rg is alkoxycarbonylaminoalkyl, and if R j is 3-isobutyl, then RJ and | do not mean methyl, or their salts, characterized in that the compound of the general formula R,) (Ri) ArOM (2) where Lg-, R, have the indicated values; M is hydrogen or alkali metal, is reacted with the compound of the general formula - (CH2) rt engsnsn / mn-s where Rj, R, JRj, Y and g have the indicated meanings} X is a hydroxylic acid; / 2. - the reactive ester ester of the hydroxyl group or XnZ together form an epoch sy-, in CJ-Cx Alkanool medium at the temperature of the reaction medium, followed by isolation of the product in free form or in the form of salt. 2. The method according to claim 1, about tl and h and w - w, and so that the compound of general formula 2 is used in the form of a phenol of metal. Sources of information taken into account in the examination: 1. US patent number 3106564, are. 26O-326.5, 1963.