Benzyl Bromide → 4-Piperidinol, 1-benzyl-4-phenyl-

HRID 238262Notes

Reaction equation

HRID 238262 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH2:14]([N:5]1[CH2:6][CH2:7][C:2]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([OH:1])[CH2:3][CH2:4]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 973334-Piperidinol, 1-benzyl-4-phenyl-Yield 62.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-4-phenylpiperidine (0.5 g, 2.8 mmol), benzylbromide (0.5 g, 3 mmol) and potassium carbonate (0.8 g, 6 mmol) were dissolved in DMF (5 mL) and stirred for 2 hours. The mixture was diluted with ethyl acetate and washed with a solution of saturated aqueous sodium carbonate solution then dried over magnesium sulphate, filtered and the solvent removed by evaporation under vacuum. The resulting solid was recrystallised from pentane to give the title compound as a white solid (0.47 g). LCMS m/z 268.3 [M+H]+. R.T.=2.37 min (Analytical Method 4).

Workup

  1. washwashed with a solution of saturated aqueous sodium carbonate solution
  2. dry with materialthen dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation under vacuum
  5. customThe resulting solid was recrystallised from pentane

Sources & evidence

ORD record
ord-3477b7c3c2d64b78b9cf4e55a4073afe
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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