Triethylamine → N-[4-(1-(2-Methoxyphenyl)-4-piperazinyl)-2-butynyl]-1,2-benzisothiazole-3-carboxamide dihydrochloride

HRID 1885313

反応式

HRID 1885313 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]([Cl:12])=[O:11])=[N:2]1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][N:24]([CH2:27][C:28]#[C:29][CH2:30][NH2:31])[CH2:23][CH2:22]1.C(N(CC)CC)C>ClCCl.O>[ClH:12].[ClH:12].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:22][CH2:23][N:24]([CH2:27][C:28]#[C:29][CH2:30][NH:31][C:10]([C:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1][N:2]=2)=[O:11])[CH2:25][CH2:26]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 153298951-(2-Methoxyphenyl)-4-(4-amino-2-butynyl)piperazineHCID 15639471Benzo[d]isothiazole-3-carbonyl chloride

生成物 1

HCID 19752299N-[4-(1-(2-Methoxyphenyl)-4-piperazinyl)-2-butynyl]-1,2-benzisothiazole-3-carboxamide dihydrochloride収率 90.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1,2-benzisothiazole-3-carboxylic acid chloride (2.0 g) and 1-(2-methoxyphenyl)-4-(4-amino-2-butynyl)piperazine (2.63 g) in dichloromethane (100 ml), was stirred while triethylamine (2.83 ml) was added dropwise. Stirring was continued overnight. After 24 hr, the reaction mixture was diluted with water and extracted with dichloromethane. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica using ethyl acetate as the eluent. The appropriate fractions were collected and concentrated. The residue was taken up in ether/dichloromethane. Ethereal hydrogen chloride was added. The precipitate was recrystallized from methanol/dichloromethane/ether to provide 2.27 g (45.7%) of product, mp 162°-164° C.

後処理

  1. additionwas added dropwise
  2. waitAfter 24 hr
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was chromatographed on silica
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated
  10. additionEthereal hydrogen chloride was added
  11. customThe precipitate was recrystallized from methanol/dichloromethane/ether

出典と根拠

ORDレコード
ord-8d5d7ed35939478fa17933ed4ec4c2fd
出典データセット
uspto-grants-1992_09
特許番号
US05143923

関連ノート

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