Potassium Iodide → HCID 67725547, compound

HRID 1734039Notes

Reaction equation

HRID 1734039 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[N:3]1.Cl[CH2:18][CH2:19][CH2:20][C:21]([C:23]1[C:27]2[C:28](=[O:33])[NH:29][CH2:30][CH2:31][CH2:32][C:26]=2[S:25][C:24]=1[CH3:34])=[O:22].[C:35](=[O:38])([O-:37])[O-].[K+].[K+].[I-].[K+].CN(C)C=[O:46]>C1(C)C=CC=CC=1.O>[C:28]([OH:33])(=[O:46])/[CH:27]=[CH:23]\[C:35]([OH:37])=[O:38].[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([N:11]2[CH2:12][CH2:13][N:14]([CH2:18][CH2:19][CH2:20][C:21]([C:23]3[C:27]4[C:28](=[O:33])[NH:29][CH2:30][CH2:31][CH2:32][C:26]=4[S:25][C:24]=3[CH3:34])=[O:22])[CH2:15][CH2:16]2)=[N:3]1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21471973HCID 21471973, compound

Product 1

HCID 67725547HCID 67725547, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 2.0 g of 4-(1,2-benzisothiazol-3-yl)piperazine hydrochloride, 2.0 g of 3-(4-chlorobutyryl)-2-methyl-5,6,7,8-tetrahydro-4H-thieno[3,2-c]azepin-4-one, 2.1 g of potassium carbonate and 1.2 g of potassium iodide in 15 ml of N,N-dimethylformamide and 15 ml of toluene was stirred at 60° C. for 3 hours. After the mixture was cooled in a water bath, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with saline solution, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on a silica gel, dissolved in isopropyl alcohol and ethanol-maleic acid was added thereto to make maleate. The resulting crystals were recrystallized from ethanol to give 0.90 g of 3-(4-(4-(1,2-benzisothiazol-3-yl) piperazin-1-yl)butyryl)-2-methyl-5,6,7,8-tetrahydro-4H-thieno[3,2-c]azepin-4-one maleate as white crystals, m.p. 150°-152° C.

Workup

  1. temperatureAfter the mixture was cooled in a water bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saline solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on a silica gel
  7. dissolutiondissolved in isopropyl alcohol
  8. additionethanol-maleic acid was added
  9. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-cf8ef10632034a1d935dbbd45318ca93
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

Loading…