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

HRID 362938Notes

Reaction equation

HRID 362938 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH:32][C:33]([NH:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:34])=[C:7]([CH:31]=1)[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:9].[OH:40]OS([O-])=O.[K+].[NH4+].[OH-]>CC#N.C(Cl)Cl.CO.O.C(Cl)Cl>[CH2:36]([NH:35][C:33](=[O:34])[NH:32][C:6]1[CH:5]=[CH:4][C:3]([S:2]([CH3:1])=[O:40])=[CH:31][C:7]=1[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14][CH2:13]1)=[O:9])[CH2:37][CH2:38][CH3:39]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 23707502Potassium hydroxy sulfite2×HCID 675956385-methylthio-2-(N'-n-butylureido)-N-[(1-diphenylme-thylpiperidin-4-yl)methyl]benzamide

Product 1

HCID 675954132-(N'-n-butylureido)-5-methylsulfinyl-N-[(1-diphenylmethylpiperidin-4yl)methyl]benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 86753736HCID 86753736, compoundSolvent

Procedure

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.

Workup

  1. washThe organic layer was washed twice with H2O
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8fd449b5d86f4c1c8b58d9037c8142e3
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

Loading…