Ammonium Chloride → N-[4-(1-hydroxyethyl)phenyl]-3-(piperidin-1-ylsulfonyl)benzamide

HRID 1967509Notes

Reaction equation

HRID 1967509 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:29])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:15]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[Cl-].[NH4+]>C(O)C>[OH:5][CH:3]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:29])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([S:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)(=[O:21])=[O:22])[CH:15]=2)=[CH:10][CH:11]=1)[CH3:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1127074N-(4-acetylphenyl)-3-(piperidin-1-ylsulfonyl)benzamideHCID 4311764Sodium borohydride

Product 1

HCID 66871890N-[4-(1-hydroxyethyl)phenyl]-3-(piperidin-1-ylsulfonyl)benzamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (8.8 mg) was added to an ethanol (2.0 mL) solution of the compound (30.0 mg) obtained in Example 92, and stirred overnight at room temperature. Aqueous saturated ammonium chloride solution was added to the reaction liquid, extracted three times with ethyl acetate, and dried with sodium sulfate. The drying agent was removed through filtration, and the solvent was evaporated off under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 80%, gradient) to give the entitled compound (29.7 mg, 98%) as a white solid.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialdried with sodium sulfate
  3. customThe drying agent was removed through filtration
  4. customthe solvent was evaporated off under reduced pressure
  5. customThe residue was purified through silica gel column chromatography (ethyl acetate/hexane=from 0% to 80%, gradient)

Sources & evidence

ORD record
ord-0e07175189e54c739a0577b72fc52c54
Source dataset
uspto-grants-2013_04
Patent number
US08420823B2

Reaction notes

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