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

HRID 487166Notes

Reaction equation

HRID 487166 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 mi of ethanol and 30 ml of water was dissolved 2.93 g of 1-acetyl-4-(4-dimethyiaminobenzoylmethyl)piperidine prepared in Example 39, and at room temperature, 1 9 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-cf3b75c033754b758c24c321fc6c8204
Source dataset
uspto-grants-1994_03
Patent number
US05294625

Reaction notes

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