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

HRID 483436Notes

Reaction equation

HRID 483436 reaction equation
[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]/[CH:28]=[CH:29]\[CH2:30][NH2:31])[CH2:23][CH2:22]1.C(N(CC)CC)C>ClCCl.O.C(=O)([O-])[O-].[Na+].[Na+]>[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]/[CH:28]=[CH: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

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 15639471Benzo[d]isothiazole-3-carbonyl chlorideHCID 67754896Z-1-(2-methoxyphenyl)-4-(4-amino-2-butenyl)piperazine

Product 1

HCID 67754721Z-N-[4-(1-(2-Methoxyphenyl)-4-piperazinyl)-2-butenyl]-1,2-benzisothiazole-3-carboxamide dihydrochlorideYield 104.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 1,2-benzisothiazole-3-carboxylic acid chloride (1.77 g) and Z-1-(2-methoxyphenyl)-4-(4-amino-2-butenyl)piperazine (2.34 g) in dichloromethane (100 ml) was stirred while triethylamine (2.51 ml) was added dropwise. Stirring was continued overnight. After 24 hr, the reaction mixture was diluted with water and saturated aqueous sodium carbonate solution and extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was taken up in dichloromethane/ether and hydrogen chloride in ether was added. The precipitate was recrystallized from methanol/dichloromethane/ether to provide 2.31 g (51.7%) of product, mp 184-187.

Workup

  1. additionwas added dropwise
  2. waitAfter 24 hr
  3. extractionextracted with dichloromethane
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. additionhydrogen chloride in ether was added
  9. customThe precipitate was recrystallized from methanol/dichloromethane/ether

Sources & evidence

ORD record
ord-e66c81035a844f1bbfa450b1996f7651
Source dataset
uspto-grants-1993_07
Patent number
US05225412

Reaction notes

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