Sodium hydride → HCID 86721897, compound

Participants

Reaction Steps

A solution of 4-isobutylsulfamoyl-benzyl-phosphonium bromide (1.87 g, 3.29 mmol) in DMF (10 mL) was treated with NaH (60% dispersion in mineral oil, 329 mg, 8.22 mmol) and stirred at room temperature for 1 hour. 1-(Methylsulfonyl)piperidin-4-one (758 mg, 4.28 mmol) was added and the mixture stirred at room temperature for 18 hours. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-100% EtOAc in cyclohexane) gave N-isobutyl-4-(1-methanesulfonyl-piperidin-4-ylidenemethyl)-benzenesulfonamide (392 mg, 31%). 1H NMR (300 MHz, CDCl3) δ 7.81 (d, J=8.2 Hz, 2H), 7.31 (d, J=8.2 Hz, 2H), 6.43 (s, 1H), 4.40 (t, J=6.5 Hz, 1H), 3.37 (t, J=5.7 Hz, 2H), 3.25 (t, J=5.8 Hz, 2H), 2.82-2.76 (m, 5H), 2.60 (t, J=5.7 Hz, 2H), 2.53 (t, J=5.7 Hz, 2H), 1.80-1.66 (m, 1H), 0.88 (d, J=6.7 Hz, 6H). LCMS (m/z, Method A) ES+ 523.1 [M+Na]+.

Provenance & Evidence