HCID 86594079, compound → HCID 86594078, compound

HRID 348539Notes

Reaction equation

HRID 348539 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:14]2[CH2:19][CH2:18][N:17]([C@@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]3[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:16][CH2:15]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)(C)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:14]2[CH2:15][CH2:16][N:17]([C@@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@@H:21]3[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:18][CH2:19]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 86594079HCID 86594079, compound

Product 1

HCID 86594078HCID 86594078, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The title compound, MS (ISP): m/e=490.3 (M+H+), was prepared by hydrogenation of (+/−)-4-nitro-N-phenyl-N-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-benzenesulfonamide according to the following procedure. (+/−)-4-Nitro-N-phenyl-N-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-benzenesulfonamide (0.05 g, 0.096 mmol) was suspended in isopropanol (3 ml) and the mixture was purged with argon. Palladium hydroxide on charcoal was added to the suspension, which was then put under a hydrogen atmosphere and stirred at room temperature for 20 h. The catalyst was then filtered off and the solvent was evaporated, leaving the title compound as a white foamy solid (0.039 g, 82%).

Workup

  1. customthe mixture was purged with argon
  2. additionPalladium hydroxide on charcoal was added to the suspension, which
  3. filtrationThe catalyst was then filtered off
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-658eedd53a5c41ec8361187b212cc944
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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