Patent GB-962793-A (GB)
Title: Improvements in or relating to pharmacologically active compounds being substituted tryptamines
Filed: 1960-07-11
Abstract: <FORM:0962793/C1/1> <FORM:0962793/C1/2> <FORM:0962793/C1/3> <FORM:0962793/C1/4> <FORM:0962793/C1/5> The invention comprises compounds of formula I and acid addition salts thereof in which R1 represents an hydroxyl group or an etherified hydroxyl group n is 0, 1, 2 or 3, R2 is a C3-8- alkyl group in which at least one hydrogen atom is replaced by a hydroxyl or an etherified or esterified hydroxyl group, and R3 is a hydrogen atom or a C1-8 alkyl group, with or without one or more hydroxyl or etherified or esterified hydroxyl groups substituted for one or more hydrogen atoms in such alkyl groups; the preparation thereof either by alkylating a compound of formula II especially with reacting the amino compound with a compound R2X (where X is a halogen atom) or with a carboxylic acid halide or anhydride comprising an acyl residue convertible by reduction to such radical R2 and where one reactant consists of such acid halide or anhydride, reducing the reaction product with a metal or metal alkyl hydride; or by reacting a compound of formula III with an aliphatic amine which is substituted by one or more esterified or etherified hydroxyl groups or by groups which, after the alkylation reaction, are replaced by esterified or etherified hydroxyl groups or when the first named reactant is a compound of the formula III except that the hydrogen atoms at one or each of the C atoms in the 3-ethyl group are replaced by oxygen, reducing the reaction product after alkylation with a metal or metal alkyl halide; or by reacting a compound of formula II with a compound of formula IV (where Hlg represents a chloride or bromine atom and R5 represents an alkyl group and n is 1 to 6 and reducing the semi-ester-semi-amide to an amino alcohol with a metal hydride or metal alkyl hydride; or by reacting a compound of formula II with a compound of formula X (wherein n1 is 2 to Y) and reducing the resulting ester to the alcohol; or with a compound Hlg(CH2)n11-O-R4 in which R4 is an alkyl, aryl or aryl or an acyl group, and n11 is 3 to 8. Benzyl ethers are hydrogenated to the free hydroxy compounds. 3-(2-Ethylaminoethyl)indole is prepared by reacting 3-(2-aminoethyl)indole with acetic anhydride and reducing the resulting 3-(2-acetamidoethyl)indole. Similarly are prepared 3-(2-R-aminoethyl)indoles where R is propyl, butyl isobutyl, amyl and isoamyl, 3-(2-ethylaminoethyl)-5-methoxy-5-benzyloxy- and 5, 6-dimethoxy-indoles through the corresponding acetyl derivatives. 1-Benzyloxy-5-bromopentane is prepared from benzyl alcohol and 1, 5-dibromopentane.  5-Methoxyindolylglyoxylic acid chloride-3 is prepared from 5-methoxyindole and oxalyl chloride. N-Ethylaminosuccinic acid dimethyl ester is prepared from dimethyl maleate and ethylamine.  2-Nitrophenetidine is diazotized and reacted with formaldoxime to give 4-ethoxy-2-nitrobenzaldehyde which is reacted with nitromethane to give 4-ethoxy-2-b -dinitrostyrene, the last named is hydrogenated to give 6-ethoxyindole and converted into 6-ethoxy indolylgyoxylic acid chloride-3 with oxalyl chloride. Pharmaceutical compositions contain at least one of the compounds of the invention and may be in the form of tablets or solutions for injection.