Production of 1-(3-hydroxy-propyl)-1,4-diazepane and 1,4-bis(3,4

Details Production of 1-(3-hydroxy-propyl)-1,4-diazepane and 1,4-bis(3,4 Production of 1-(3-hydroxy-propyl)-1,4-diazepane and 1,4-bis(3,4

1985-01-22

1988-06-14

Hollrah, Glennon H.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540574, 574399, 574365, 558455, C07D24308

Patent

active

047512989

ABSTRACT:
There is disclosed a process for the production of 1,4-bis-[3-(3,4,5-trimethoxybenzyloxy)-propyl]-diazepane which consists of first reacting 3-aminopropanol with acrylonitrile and subsequently reacting in aqueous solution with formaldehyde and hydrocyanic acid or with formaldehyde and an alkali cyanide in the presence of alkali hydrogen sulfite to form cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amine; hydrogenating the thus obtained reaction product in the presence of a hydrogenating catalyst and ammonia to 1 (3-hydroxy-propyl)-1,4-diazepane and reacting the latter compound for example with 3-halogen propanol or with allyl alcohol and introducing two 3,4,5-trimethoxy-benzoyl groups into the thus obtained reaction product by esterification.

REFERENCES:
patent: 3532685 (1970-10-01), Arnold
patent: 4068069 (1978-01-01), Kato
Poppeldorf, J. Org. Chem. 26, 131-134 (1961).
Kotelko, Acta Polon. Pharm. 18 171-2 (1961) Abstract.
Kotelko, Acta Polon. Pharm. 19, 215-221 (with English Trans.).
Organic Reactions, pp. 205, 239, vol. 12.

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