Diisopropylethylamine → (1-(1-Methyl-1H-Imidazol-4-ylsulfonyl)Piperidin-4-yl)(Phenyl)Methanone

Participants

Reaction Steps

To a solution of 4-benzoylpiperidine hydrochloride (1.50 g, 6.64 mmol) and DIPEA (2.74 mL, 15.3 mmol) in CH2Cl2 (35 mL) was added 1-methylimidazole-4-sulfonyl chloride (1.31 g, 7.31 mmol) and stirred for 18 h. The reaction was washed with 2 N NaOH (30 mL), dried over MgSO4 and concentrated under vacuum to afford 4 as a white solid (2.05 g, 93%); 1H-nmr (400 MHz, CDCl3) δ 7.81-7.78 (m, 2H), 7.52-7.36 (m, 5H), 3.86-3.78 (m, 2H), 3.71 (s, 3H), 3.26-3.17 (m, 1H), 2.82 (td, J=11.0, 3.0 Hz, 2H), 1.92-1.84 (m, 4H); m/z 334.0 [M+H].

Provenance & Evidence