Acetic Anhydride → HCID 86594092, compound

HRID 348550Notes

Reaction equation

HRID 348550 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:12]2[CH2:17][CH2:16][N:15]([C@@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(O)(=O)C>[C:30]1([N:11]([CH:12]2[CH2:13][CH2:14][N:15]([C@@H:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]3[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:16][CH2:17]2)[S:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:36](=[O:38])[CH3:37])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86594078HCID 86594078, compound

Product 1

HCID 86594092HCID 86594092, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (+/−)-4-amino-N-phenyl-N-[cis-1-(2-phenyl-cyclohexyl)-piperidin-4-yl]-benzenesulfonamide (0.1 g, 0.2 mmol) in acetic acid (5 ml) was treated with acetic anhydride (1 ml) and stirred at room temperature for 1 h. The volatiles were evaporated and the residue was purified by flash chromatography on silica gel, eluting with dichloromethane/methanol/ammonia 110:10:1. The product was crystallised from hexane/ether, yielding the title compound (0.06 g, 59%) as a white solid, MS (ISP): m/e 532.5 (M+H+).

Workup

  1. customThe volatiles were evaporated
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with dichloromethane/methanol/ammonia 110:10:1
  4. customThe product was crystallised from hexane/ether

Sources & evidence

ORD record
ord-867073a564a548c389e3cc3485f76e7f
Source dataset
uspto-grants-2007_02
Patent number
US07176316B2

Reaction notes

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