Potassium Iodide → HCID 21472080, compound

HRID 1734040Notes

Reaction equation

HRID 1734040 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][C:20]([C:22]1[C:26]2[NH:27][C:28](=[O:32])[CH2:29][CH2:30][CH2:31][C:25]=2[S:24][C:23]=1[CH3:33])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1.O>[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][C:20]([C:22]3[C:26]4[NH:27][C:28](=[O:32])[CH2:29][CH2:30][CH2:31][C:25]=4[S:24][C:23]=3[CH3:33])=[O:21])[CH2:15][CH2:16]2)=[N:3]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochlorideHCID 21471943HCID 21471943, compound

Product 1

HCID 21472080HCID 21472080, compoundYield 38.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 2.1 g of 4-(1,2-benzisothiazol-3-yl)piperazine hydrochloride, 2.0 g of 3-(3-chloropropionyl)-2-methyl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-one, 2,2 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 5 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 crystallized from isopropyl alcohol-isopropyl ether. The resulting crystals were recrystallized from ethanol to give 1.30 g of 3-(3-(4-(1,2-benzisothiazol-3-yl)piperazin-1-yl)propionyl)-2-methyl-4,6,7,8-tetrahydro-5H-thieno[3,2-b]azepin-5-one as white crystals, m.p. 146°-147° 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. customcrystallized from isopropyl alcohol-isopropyl ether
  9. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-b526473f1120444faf713dd4b6fd3359
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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