Diisopropylethylamine → HCID 24703350, compound

Participants

Reaction Steps

To a solution of 4-piperidone monohydrate hydrochloride (1.0 g, 6.5 mmol) in methylene chloride (32 mL) at rt were successively added DIPEA (1.4 mL, 7.8 mmol) and 2,6-difluorobenzoyl chloride (0.82 mL, 6.5 mmol). The resulting heterogeneous mixture was stirred at rt for 2 d. The resulting mixture was washed with 1 N aq. sodium hydroxide (3×10 mL) and the combined basic aqueous portion was back-extracted with methylene chloride (2×10 mL). The organic extracts were combined and washed with 10% aq. citric acid (2×10 mL), brine (20 mL), and dried over anhyd sodium sulfate. Concentration under vacuum afforded the title compound a as a pale yellow solid (1.29 g, 83%). 1H NMR (400 MHz, d3-MeOD): δ 7.60 (m, 1H), 7.18-7.09 (m, 2H), 4.09 (t, J=6.4 Hz, 2H), 3.70 (t, J=6.3 Hz, 2H), 2.62 (t, J=6.4 Hz, 2H), 2.48 (t, J=6.3 Hz, 2H).

Provenance & Evidence