N-(4-Hydroxybenzyl)-3,4,5-trimethoxybenzamide and method for pro

Details N-(4-Hydroxybenzyl)-3,4,5-trimethoxybenzamide and method for pro N-(4-Hydroxybenzyl)-3,4,5-trimethoxybenzamide and method for pro

1982-08-31

1985-03-26

Waltz, Thomas A.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564176, C07C10344, C07C10200

Patent

active

045074992

ABSTRACT:
The invention relates to a method for producing trimethobenzamide chlorohydrate.
According to such a method, a chloromethilation is carried out on anisle and, after reaction with urotropine followed by acidic hydrolisis, 4-methoxybenzylamide chlorohydrate is obtained which, demethyilated by hydrazoic acid, provides 4-hydroxy benzylamine chlorohydrated that, reacted with 3,4,5-trimethoxybenzoic acid chloride, provides N-(4-Hydroxybenzyl)-3,4,5-trimethoxybenzamide. The latter is per se a novel compound and is also the subject of the invention. This compound is reacted with sodium hydride and N,N-dimethylamino ethyl chloride to provide base trimethobenzamide, the latter being salified with hydrochloric acid.

REFERENCES:
patent: 2879293 (1959-03-01), Goldberg et al.
patent: 3083140 (1963-03-01), Testa
patent: 3481980 (1969-12-01), Teitel et al.
March, Advanced Organic Chemistry, 2nd ed., pp. 378-379, McGraw-Hill.
Buehler et al., Survey of Organic Syntheses, p. 452, Wiley-Interscience.

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