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Water → HCID 9823929、化合物

HRID 1596036
ノート
印刷プレビュー

反応式

HRID 1596036 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([N:25]([CH3:27])[CH3:26])[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[OH:24].CC([O-])(C)C.[K+].O>CS(C)=O>[ClH:1].[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:24][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:18]1[CH:17]([N:25]([CH3:27])[CH3:26])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[Cl:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 119062-Chlorobenzyl chlorideHCID 21705657HCID 21705657、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 9823929HCID 9823929、化合物収率 12.6%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

902 mg (5.60 mmole) of 2-chlorobenzyl chloride and 1.0 g (3.73 mmole) 2-[(2-chlorophenyl)dimethylaminomethyl]-cyclohexanol were dissolved in 6.0 ml dimethylsulfoxide, analytical grade, 503 mg (4.48 mmole) solid potassium tert-butylate were added, under nitrogen, and the mixture was heated at 100° C. for 15 hours. For working up, 10 ml water were added, and the mixture was extracted three times with 15 ml ether each time. The combined extracts were washed with 10 ml each of potassium hydroxide solution (2 M) and water and extracted three times with 25 ml hydrochloric acid (5 wt. %) each time. The combined acid extracts were rendered alkaline (pH≧11) with sodium hydroxide solution (32 wt. %) and extracted three times with 25 ml methylene chloride each time. The combined organic extracts were dried over sodium sulfate, filtered and concentrated on a rotary evaporator (500 to 10 mbar). 277 mg crude base were obtained. 151 mg {[2-(2-chlorobenzyloxy)cyclohexyl]-(2-chlorophenyl)methyl}-dimethylamine hydrochloride (9.4% of theoretical) with a melting range of 108-100° C. were obtained from this crude base in accordance with Example 1 (4th stage) using chlorotrimethylsilane/water in 2-butanone.

後処理

  1. extractionthe mixture was extracted three times with 15 ml ether each time
  2. washThe combined extracts were washed with 10 ml each of potassium hydroxide solution (2 M) and water
  3. extractionextracted three times with 25 ml hydrochloric acid (5 wt. %) each time
  4. extractionextracted three times with 25 ml methylene chloride each time
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator (500 to 10 mbar)
  8. custom277 mg crude base were obtained

出典と根拠

ORDレコード
ord-ae7df967d9134cb58aecfbfc30115dbc
出典データセット
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06288278B1

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート