Hydrochloric Acid → HCID 19981495, compound

Participants

Reaction Steps

Ethyl 6,6-diphenyl-8-dimethylaminononanoate (863 mg) was taken up in methanol (7 ml) and treated with 1M KOH in methanol (7.4 ml). The mixture was refluxed under Ar for 2.5 hours, and cooled. The pale yellow solution was concentrated to dryness to provide a clear pale yellow glass. The residue was taken up in H2O (2 ml) and treated dropwise with 1N HCl to pH 6. This solution was then evaporated to dryness and dissolved in 12 ml of methanol to yield a precipitate which was filtered. This procedure was repeated, using 8 ml of methanol, and the filtrates were evaporated to dryness. A 250 mg portion, dissolved in methanol (12 ml), was purified by PTLC. Development with 30% methanol/CHCl3 produced a major band (Rf range 0.12-0.31), which was scraped off the plate and eluted with methanol. The methanolic extracts were evaporated, and the residue was coevaporated twice with toluene (3 ml) to yield 167 mg of 6,6-diphenyl- 8-dimethylaminononanoic acid, as a clear oil.

Provenance & Evidence