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

HRID 1885313

반응식

HRID 1885313 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8d5d7ed35939478fa17933ed4ec4c2fd
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05143923

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