Methanol → 4-Piperidinol, 1-benzyl-4-phenyl-

HRID 238264Notes

Reaction equation

HRID 238264 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](F)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC([O:24]C(Cl)=O)C.CO>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([OH:24])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67059915HCID 67059915, compound

Product 1

HCID 973334-Piperidinol, 1-benzyl-4-phenyl-Yield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-benzyl-4-fluoro-4-phenyl-piperidine (0.22 g) in dry DCM (5 mL) was added 1-chloroethylchloroformate (1 mmol). The mixture was stirred for 1 hour and then methanol (5 mL) was added and the mixture stirred overnight. The solvent was removed under vacuum, and the resulting solid triturated from diethyl ether to give the title compound as a white solid (0.12 g). LCMS m/z 180.1 [M+H]+. R.T.=2.27 min (Analytical Method 4).

Workup

  1. stirringthe mixture stirred overnight
  2. customThe solvent was removed under vacuum
  3. customthe resulting solid triturated from diethyl ether

Sources & evidence

ORD record
ord-58411a10c2db403f87882eee465cf485
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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