Phosphate → HCID 10822170, compound

Participants

Reaction Steps

2-(1-Methylpyrrol-2-yl)ethylamine (4.96g, 0.04m) and triethylamine (5.6mL, 0.04m) were stirred together in toluene (60mL). A solution of ethyl 5-bromopentanoate (7.80g, 0.04m) in toluene (20 mL) was added dropwise over 1 hr at room temperature. The reaction mixture was heated with stirring at 70 degrees overnight. The reaction was worked up by addition of a phosphate buffer until a pH of 5-6 was reached; the reaction mixture was then diluted with ether and the layers were separated. The aqueous layer was exhaustively washed with diethyl ether. The combined organic layers were washed with water, brine and then dried over anhydrous potassium carbonate. The dryinq agent was filtered away, and the filtrate was concentrated to a light yellow solid weighing 5.2g. It was recrystallized from methylene chloride/hexane to give 4.2g (51.2%) of purified title compound.

Provenance & Evidence