Ethanol → 1-Acetyl-4-[2-hydroxy-2-(4-dimethylaminophenyl)ethyl]piperidine

HRID 1645871Notes

Reaction equation

HRID 1645871 reaction equation
C(O)C.[C:4]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH2:9][CH2:8]1)(=[O:6])[CH3:5].[BH4-].[Na+]>ClCCl.O>[C:4]([N:7]1[CH2:12][CH2:11][CH:10]([CH2:13][CH:14]([OH:24])[C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH3:22])[CH3:23])=[CH:19][CH:20]=2)[CH2:9][CH2:8]1)(=[O:6])[CH3:5]

Participants

6

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 193908471-Acetyl-4-(4-dimethylaminobenzoylmethyl)piperidine

Product 1

HCID 193908481-Acetyl-4-[2-hydroxy-2-(4-dimethylaminophenyl)ethyl]piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In a solvent mixture of 60 ml of ethanol and 30 ml of water was dissolved 2.93 g of 1-acetyl-4-(4-dimethylaminobenzoylmethyl)piperidine prepared in Example 39, and at room temperature, 1 g of sodium borohydride was gradually added. The reaction mixture was diluted with dichloromethane and water for distribution and the dichloromethane layer was dried over anhydrous magnesium sulfate. The solvent was then distilled off and the oily residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give a pale yellow solid melting at 119°-120° C.

Workup

  1. dry with materialthe dichloromethane layer was dried over anhydrous magnesium sulfate
  2. distillationThe solvent was then distilled off
  3. customthe oily residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-41559a2359ca4016b3421e0fc5928e0d
Source dataset
uspto-grants-1993_01
Patent number
US05177087

Reaction notes

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