Ammonium Hydroxide → 2-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide

Participants

Reaction Steps

A solution of 5-methylthio-2-(N'-n-butylureido)-N-[(1-diphenylme-thylpiperidin-4-yl)methyl]benzamide (EXAMPLE 73) (200 mg, 0.367 mmol) in CH3CN/CH2Cl2 /MeOH/H2O (10 ml/2 ml/4 ml/0.5 ml) was agitated with OXONE® (2KHSO5KHSO4K2SO4) (142 mg, 0.231 mmol) for 2 hours at room temperature and then an additional OXONE® (15 mg) was added. The reaction mixture was made basic with 25% NH4OH and diluted with CH2Cl2. The organic layer was washed twice with H2O, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel to give 2-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide. 130 mg (63%): mp 209°-211° C.; 1H NMR (CDCl3) ppm: 0.91 (3H, t), 1.33-1.88 (11H, m), 2.69 (3H, s), 2.88 (2H, m), 3.22-3.31 (4H, m), 4.24 (1H, s), 4.85 (1H, bt), 7.03 (1H, bt), 7.13-7.42 (11H, m), 7.91 (1H, d), 8.63 (1H, d), 10.71 (1H, s); and 2-(N'-n-butylureido)-5-methylsulfonyl-N-[(1-diphenylmethylpiperidin-4-yl)-methyl]benzamide, 30 mg (14%): mp 178°-179° C.; 1H NMR (CDCl3) ppm: 0.93(3H, t), 1.31-1.88 (11H, m), 2.90 (2.90 (2H, m), 3.02 (3H, s), 3.23-3.34 (4H, m), 4.25 (1H, s), 4.79 (1H, bt), 6.61 (1H, bt), 7.13-7.40 (10H, m), 7.89 (1H, dd), 7.97 (1H, d), 8.73 (1H, d), 10.82 (1H, s), respectively.

Provenance & Evidence