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Hydrochloric Acid → gamma-[4-(p-Chloro-alpha-hydroxybenzyl)piperidino]-p-fluorobutyrophenone

HRID 866868
ノート
印刷プレビュー

反応式

HRID 866868 の反応式
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH:21]([C:24](=[O:32])[C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=4)[CH2:20][CH2:19]3)OCC[O:11]2)=[CH:6][CH:5]=1.C(O)C.Cl>O.[OH-].[Na+]>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:24]([CH:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][C:10](=[O:11])[C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=3)[CH2:19][CH2:20]2)[OH:32])=[CH:26][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 20318878HCID 20318878、化合物

生成物 1

HCID 11474752gamma-[4-(p-Chloro-alpha-hydroxybenzyl)piperidino]-p-fluorobutyrophenone

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 14798
Sodium Hydroxide
溶媒

実験手順

Sodium borohydride (0.4 g., 0.01 mole) was added in small portions to a stirring solution of 2.2 g. (0.0052 mole) of 2-(p-fluorophenyl)-2-{3-[4-(p-chlorobenzoyl)piperidino]propyl}-1,3-dioxolane in 20 ml. of absolute ethanol. The reaction mixture was stirred until gas evolution ceased and then dilute hydrochloric acid was added dropwise until an acidic solution was obtained. After stirring overnight the mixture was diluted with water and basified with dilute sodium hydroxide. The free base was extracted into chloroform, the chloroform solution was washed with water, dried over magnesium sulfate, filtered, and the filtrate concentrated under vacuum. The residual oil crystallized on trituration with isopropyl ether to give 1.2 g. (60%) of a light brown solid which melted at 143°-146° C. Recrystallization of the solid from benzene-isooctane gave 0.8 g. of a white powdery solid which melted at 146.5°-147° C.

後処理

  1. customwas obtained
  2. stirringAfter stirring overnight the mixture
  3. extractionThe free base was extracted into chloroform
  4. washthe chloroform solution was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe residual oil crystallized on trituration with isopropyl ether
  9. customto give 1.2 g
  10. customRecrystallization of the solid from benzene-isooctane
  11. customgave 0.8 g

出典と根拠

ORDレコード
ord-f96c1814ecd54507b6ba3a91f441e32b
出典データセット
uspto-grants-1978_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04101662

反応ノート

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