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

HRID 46459

반응식

HRID 46459 반응식
[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

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 12679HexamethylphosphoramideHCID 236603BromodiphenylmethaneHCID 516893Potassium Bicarbonate

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-296c1f3357a0401ba648a59243356390
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04173566

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