SU637078A3 - Method of obtaining amines or salts thereof - Google Patents

Description

(54) THE METHOD OF OBTAINING AMINES OR THEIR SALTS is reacted with a compound of the general formula 2 - ' - (" Ng) n-tg where Rg, R4, Rs, Y and n are as defined above; Z - reactionary ester hydroxy group etherified into ester, at 80-130 ° С in С-Сз-alkanol medium. The reaction can be carried out in the presence of a base. Suitable bases are, for example, alkali metal alcoholates, preferably sodium or potassium alcoholate, or alkali metal carbonates, for example sodium or potassium carbonate. The target products are obtained in free form or in the form of their acid addition salts. Example. The south of simple 2-allylphenylglipidyl ether in 100 ml of ethanol is saturated with ammonia gas and the mixture is heated in an autoclave on a boiling water bath for 4 hours. Then the solvent is evaporated and the residue containing 1-amino-3- (2-allnlphenoxy) propanol 2, is dissolved in ethnyl acetate and gaseous hydrogen chloride is passed. The crystallized hydrochloride is then filtered and dissolved in 60 ml of ethanol, after which 15 g of 2- (4-carbamylphenoxy) ethyl iodide and 20 g of potassium carbonate are added. The mixture is heated in an autoclave at 120 ° C for 10 hours, then the solvent is evaporated and 100 ml of 2N is poured to the residue. hydrochloric acid and 100 ml of ether. The aqueous phase is separated, alkalinized 2 and. sodium hydroxide and extracted with ethyl cepate. The ethyl acetate phase is dried over potassium carbonate, after which the hydrochloride is precipitated with gaseous hydrogen chloride. Hydrochloride (4-carbamylphenoxy) -ethylamino -3 - (2-allylphenoxy) -propanol-2 is obtained, m. Pl. 211 ° C (61% yield). Example 2. 10 g of simple 2-allylphenylglycidyl-OEOH ether in 100 ml of methapol is saturated with gaseous ammonia and the mixture is heated in an autoclave and a boiling water bath for 4 hours. After cooling, 2- (4-carbamylphenoxy) ethyl iodide is added and the mixture is heated for 15 h. 80 ° C. Then the solvent is evaporated and the residue is mixed with 100 ml of 2 p. Hydrochloric acid and 100 ml of ether. The aqueous phase is separated, alkalinized with 2 hydrochloric acid and extracted with ethyl acetate. Egplacetpuyu phase is dried over the capcoate cacc, after which the hydrochloride oride precipitated gaseous - -. .-, "". ". ,,,,, I 1. -V -т: rii (Л I: .Г G., Ч.Т Г 7 т Т о (4-carbamylphenoxy) -ethylamino-3- (2-allylphenoxy) -propanol chloride) 2 melts at 211 ° C. (yield 56% of theory). Example 3. The south of simple 2-allylphenylglycidyl ether in 100 liters of ethanol is saturated with gaseous ammonia and the mixture is heated in an autoclave on a boiling water bath for 4 hours. Then the solvent is evaporated and the residue containing 1-amino3- (2-allylphenoxy) -propanol-2 is dissolved in ethyl acetate and hydrogen chloride gas is passed in. The crystallized hydrochloride is filtered and dissolved in 60 ml of isopropanol and then 15 g of 2- (4-carbamylphenoxy) ethyl iodide and 20 g of potassium carbonate are added.The mixture is heated for 9 hours at 130 ° C. The solvent is evaporated and 100 ml of 2N hydrochloric acid and 100 ml of ether are added to the residue. The aqueous phase is separated, made alkaline with 2N sodium hydroxide and extracted with ethyl acetate. The ethyl acetate phase is dried over cahl carbonate, and the hydrochloride is precipitated with gaseous hydrogen chloride. melts at 211 ° C (68% yield). Analogously to Examples 1-3, the following compounds are obtained: (4-carbamylphenoxy) ethylamino-3- (2-chloro-5-methylphenoxan) propanyl-2 hydrochloride, yield 59%, mp. 250 ° C (with decomp.); 1 - 1-methyl-2- (4-carbamylfsioxy) ethyleneamino-3- (2-allylphenoxy) -propanol-2 hydrochloride, t. pl. 94 ° C, yield 67%; 1- 1-methyl-2 - (2-methylphenox) -ethylamino-3- (2-allylphenoxy) pronanol-2 hydrochloride, t. pl. 142 ° C, yield 63% (structure confirmed by NMR spectrum); hydrochloride 1-. 1-methyl-2- (4-methylphenoxy) -lamp-3- (2-allylphenoxy) -propanol-2, so pl. 146 ° C, yield 62% (structure confirmed by NMR spectrum); - methyl-2- (4 - carbamoylphenoxy) ethylamino-3 - (3-methylpzonitrosomethylphenoxy) propanol-2, t. pl. 106 ° C (HC1), yield 58% (structure confirmed by NMR); 1- (4-2- 2-methoxycarbonnlamino (ethyl) fe1-yuxi-et11lamino | -3 - (2-methylphenoxy) propanol-2 as base, mp 93 ° C, yield 61% (structure confirmed by NMR spectrum) -; (4-carbamylphenoxy) -ethylAlino-3 (3-al, p11) -nopaiol-2, so nl 228 ° C (as hydrochloride), yield 58% (structure confirmed by NMR spectrum). p ivi in l and l of the invention 1. Method of obtaining total amyoosis , Cr-C3-alkoxyalkoxy, alkoxycarbonylaminoalkoxy with 3-9 carbon atoms in alkoxy groups,

HOCHsCHaNHCOCHs-O-,

CHaOCHsCH NH-COCHN-O-

and,

where R is hydrogen or alkyl with 1 to 3 carbon atoms;

R2 is hydrogen, halogen; Ra and R4 are hydrogen and methyl;

Rs is hydrogen, alkoxycarbonylaminoalkyl with 2-5 carbon atoms in the alkyl and alkoxy groups, cyaine group, -CONRsR, where Re and RT are hydrogen or Re and R together with the nitrogen atom linked to them form a morpholine ring;

Y is an oxygen atom and methylene;

n is an integer from 0 to 5;

Ar - phenyl draw,

moreover, if Y is methylene, then n is 1-5, if RI is methyl, then it is not bound to phenyl in position 2, except when Rs is alkoxycarbonylaminoalkyl, and if RI is 3-isobutyl, then Rs and R4 does not mean methyl.

THEY RS

I r4

Claims (2)

I H or salts thereof, characterized in that the compound of the general formula he n i i (P) (KI) (R AG OCH 2 CH SINN Where Ar, RI and Ra are as defined above, subjected to interaction with the compound of the General formula Z-C- (Cli2) n-Y III r4 where RS, Ri, Rs, Y and tt are as defined above; Z is a reactive esterified ester into a hydroxyl group, at 80-130 ° C in a C-C3-alkanol medium, followed by isolation of the target product in free form or as a salt. 2. A method according to claim 1, characterized in that the reaction is carried out in the presence of a base. The source of information taken into account in the examination: 1. The patent of England No. 1079534, cl. C 07 C, publ. 08.16.67