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

HRID 46459

反応式

HRID 46459 の反応式
[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

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 12679HexamethylphosphoramideHCID 236603BromodiphenylmethaneHCID 516893Potassium Bicarbonate

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-296c1f3357a0401ba648a59243356390
出典データセット
uspto-grants-1979_11
特許番号
US04173566

関連ノート

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