1-Benzyl-4-piperidone → 1-Benzyl-4-(4-methoxyphenyl)piperidin-4-ol

HRID 1429220Notes

Reaction equation

HRID 1429220 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([N:18]1[CH2:23][CH2:22][C:21]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([OH:24])[CH2:20][CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 178491912HCID 178491912, compound

Product 1

HCID 159073291-Benzyl-4-(4-methoxyphenyl)piperidin-4-olYield 44.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(4-Methoxyphenyl)magnesium bromide (0.5 M in THF, 90 mL, 45.0 mmol) was added slowly (˜25 minutes) via cannula to a cold (0° C.) solution of 1-benzylpiperidin-4-one (5.4 mL, 30.2 mmol) in THF (60 mL). The reaction was stirred at 0° C. under nitrogen for 2 hours. The reaction was quenched with saturated aqueous NH4Cl then diluted with ether. The organic fraction was washed with saturated aqueous NH4Cl (2×) brine (1×) and concentrated. Purification using flash chromatography (5-100% EtOAc/hexane) provided 4.02 g (44%) of the titled compound. MS (DCI) m/z 298 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. additionthen diluted with ether
  3. washThe organic fraction was washed with saturated aqueous NH4Cl (2×) brine (1×)
  4. concentrationconcentrated
  5. customPurification

Sources & evidence

ORD record
ord-4a393c7977714b27877c81d0e7b42524
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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