Trifluoroacetic acid → HCID 58996649, compound

Participants

Reaction Conditions

Reaction Steps

1-Boc-4-(2-aminomethyl-phenyl)-piperazine (0.75 g, 2.6 mmol) was dissolved in methylene chloride (20 mL), treated with DIPEA (2.3 mL, 13 mmol), and cooled to about 0° C. Propionyl chloride (0.20 mL, 2.34 mmol) was added and the mixture was stirred for about 1 hour at 0° C. and subsequently stirred overnight at r.t. The mixture is diluted with ethyl acetate (400 mL), washed with water (45 mL), saturated aqueous sodium bicarbonate (45 mL) and brine (45 mL), and then dried over anhydrous sodium sulfate. Concentration under reduced pressure followed by silica gel chromatography (50% ethyl acetate in hexanes) gave an oil, which was dissolved in methylene chloride (10 mL). The mixture was stirred with TFA (10 mL) for about 1.5 hours. The mixture was concentrated under reduced pressure, and the residue taken up in water (25 mL). Sodium hydroxide (1.0 g, 25 mmol) and ethyl acetate (25 mL) were added and the mixture was stirred for about 45 minutes. The organic phase was collected and the aqueous phase was extracted with ethyl acetate (45 mL). The combined organic fractions were washed with water (20 mL) and brine (20 mL) and then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to yield the title compound (0.26 g, 40%) as a clear oil.

Provenance & Evidence