Potassium Carbonate → (1-Benzhydrylpiperidin-4-yl)methanol

HRID 1978337Notes

Reaction equation

HRID 1978337 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1.Br[CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH:11]([N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][OH:9])[CH2:4][CH2:3]1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 24191744(Piperidin-4-yl)methanol--hydrogen chloride (1/1)

Product 1

HCID 21993744(1-Benzhydrylpiperidin-4-yl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 20 ml of N,N-dimethylformamide, 2.291 g (15.108 mM) of 4-piperidylmethanol hydrochloride, 4.48 g (18.1 mM) of bromodiphenylmethane, and 6.26 g (45.3 mM) of potassium carbonate were stirred together at 100° C. for 3.5 days and, then, at 150° C. for 2 hours. After cooling to room temperature, this reaction mixture was poured in water and extracted with 2 portions of ethyl acetate. The organic layers were pooled and dried over MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1 to 1/1) to provide the title compound.

Workup

  1. extractionextracted with 2 portions of ethyl acetate
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1 to 1/1)

Sources & evidence

ORD record
ord-70f9d12883354bacacc5daca5e4fa1ef
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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