Production of 1-(3-hydroxy-propyl)-1,4-diazepane and 1,4-bis(3,4,5-trimethoxy-benzoyloxy)-propyl-diazepane derivatives thereof

US4751298A · kind A · utility

Assignee

• Degussa AG · DE

Inventors

• Axel Kleemann · Hanau, DE
• Bernd Lehmann · Cologne, DE
• Klaus Deller · Großkrotzenburg, DE

Key dates

• Filing date: Jan 22, 1985
• Grant date: Jun 14, 1988
• Expiry date: Jan 22, 2005

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D243/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

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.