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

HRID 1756676Notes

Reaction equation

HRID 1756676 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 distiribution 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-3469a6ad8bae4a7e8c528a5918b22ce5
Source dataset
uspto-grants-1995_08
Patent number
US05441967

Reaction notes

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