Acetonitrile → 1-Benzhydryl-2-(alpha-hydroxybenzyl)piperidine

HRID 46459

Reaction equation

HRID 46459 reaction equation
[CH:1](Br)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](=[O:18])(O)[O-].[K+].[C:20](#N)[CH3:21].[CH3:23][N:24]([CH3:33])P(N(C)C)(N(C)C)=O>O>[CH:1]([N:24]1[CH2:33][CH2:6][CH2:5][CH2:4][CH:23]1[CH:15]([OH:18])[C:21]1[CH:20]=[CH:3][CH:2]=[CH:1][CH:8]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 12679HexamethylphosphoramideHCID 236603BromodiphenylmethaneHCID 516893Potassium Bicarbonate

Product 1

HCID 203452801-Benzhydryl-2-(alpha-hydroxybenzyl)piperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reflux under an inert atmosphere for 190 hrs. a stirred suspension of 1.89 g. of erythro-α-(2-piperidyl)phenylmethanol, 2.25 g. of benzhydryl bromide, and 1.00 g. of potassium bicarbonate in 100 ml. of dry acetonitrile containing 14 ml. hexamethylphosphoramide. Cool to room temperature, pour into water, and extract with ether. Wash the extract successively with water and brine and dry over anhydrous sodium sulfate. Acidify the dry ether solution with 4.4 ml. of 1.9 M ethereal HCl. Filter and wash the resultant precipitate with acetone to obtain the analytically pure hydrochloride salt of the title compound, m.p. 232.5°-234° dec.

Workup

  1. temperatureReflux under an inert atmosphere for 190 hrs
  2. additiona stirred suspension of 1.89 g
  3. extractionextract with ether
  4. washWash the
  5. extractionextract successively with water and brine
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationFilter
  8. washwash the resultant precipitate with acetone

Sources & evidence

ORD record
ord-296c1f3357a0401ba648a59243356390
Source dataset
uspto-grants-1979_11
Patent number
US04173566

Linked notes

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