Process for the synthesis of the N-methyl-3,4-dimethoxyphenyleth

Details Process for the synthesis of the N-methyl-3,4-dimethoxyphenyleth Process for the synthesis of the N-methyl-3,4-dimethoxyphenyleth

1990-03-30

1991-10-15

Raymond, Richard L.

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

Organic compounds

Amino nitrogen containing

549513, 549519, 564374, 564384, 564385, 564389, 568435, C07C20928

Patent

active

050576240

ABSTRACT:
New process for the synthesis of the N-methyl-3,4-dimetoxyphenylethylamine of formula ##STR1## intermediate in the synthesis of the drug internationally known as verapamil. The process starts from the 3,4-dimethoxybenzaldehyde which, by means of a Darzens condensation, gives an epoxyester that, by alkaline hydrolysis and subsequent decarboxylation, gives the 3,4-dimethoxyphenylacetaldehyde. This aldehyde gives the amine of formula I by reaction with monomethylamine followed by reduction with sodium borohydride.

REFERENCES:
patent: 3894051 (1978-07-01), Suh
patent: 3997608 (1976-12-01), Suh
The Merck Index, 10th Edition, "Darzens Condensation" p. ONR-22(1983).
M. S. Newman and B. J. Magerlein (1949) in Organic Reactions, vol. V, p. 413.
The Merck Index (1983) Tenth Ed., Merck and Co., Inc., Rahway, N.J., p. 864.
Aldrich Chemical Catalogue (1990-1991), pp. 490, 494 and 495.
Chemical Abstracts, vol. 87, 1977, Abstract No. 87:134467n.

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