Ethanol → [3-(Methylamino)propyl]triphenylphosphonium Bromide Hydrobromide

Participants

Reaction Conditions

Reaction Steps

(3-bromopropyl)(triphenyl)phosphonium bromide (5.7 g, 12 mmol) was treated with 33% methylamine in ethanol (40 mL, 400 mmol) in a sealed tube. The mixture was heated at 100° C. for 1.5 hours and cooled to room temperature. The volatiles were removed, and the resultant semi-solid was taken up in methanol (23 mL) and heated at 50° C., at which point all the solids dissolved. The temperature was lowered to 40° C., and methyl t-butyl ether (68 mL) was added drop wise, giving a slurry. The slurry was cooled to room temperature and filtered, washing the product cake with methyl t-butyl ether (20 mL) to afford the title compound (4.0 g) in a 66% yield as a white solid.

Provenance & Evidence