Homoveratrylamine → HCID 178490341, compound

Participants

Reaction Steps

275 mg 4-(7-chloroquinolin-4-ylamino)-cyclohexanone (see Example 124) and 181 mg of homoveratrylamine were boiled at reflux for 3 hours in 5 ml of ethanol in the presence of molecular sieve. The solution, which was cooled and freed from the molecular sieve, was concentrated to dryness. The residue was again taken up in 5 ml of ethanol and treated under argon at +5° C. with 37 mg of sodium borohydride. After 1 hour the mixture was concentrated and the residue was suspended in dichloromethane. The excess reducing agent was decomposed by the addition of 2 ml of 3N sodium hydroxide solution. The mixture was diluted with water and the dichloromethane was separated. The dried organic phase was concentrated. The residue was chromatographed on silica gel with dichloromethane/methanol (3:1). The free base obtained was crystallized as the dihydrochloride by treatment with 3N hydrochloric acid in methanol. Yield: 280 mg (54%) of white crystals, m.p. 210° C.

Provenance & Evidence