Potassium Iodide → 7-(4-(4-(1,2-benzisothiazol-3-yl) piperazin-1-yl)butyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one oxalate

HRID 1734038Notes

Reaction equation

HRID 1734038 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[S:32][C:31]2[S:30][CH2:29][CH2:28][NH:27][C:26](=[O:33])[C:25]=2[CH:24]=1)=[O:22].[C:34](=[O:37])([O-:36])[O-].[K+].[K+].[I-].[K+].CN(C)C=[O:45]>C1(C)C=CC=CC=1.O>[C:26]([OH:33])(=[O:45])[C:34]([OH:36])=[O:37].[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[S:32][C:31]4[S:30][CH2:29][CH2:28][NH:27][C:26](=[O:33])[C:25]=4[CH:24]=3)=[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 21472056HCID 21472056, compound

Product 1

HCID 677441507-(4-(4-(1,2-benzisothiazol-3-yl) piperazin-1-yl)butyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one oxalate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 1.0 g of 4-(1,2-benzisothiazol-3-yl)piperazine hydrochloride, 1.5 g of 7-(4-chlorobutyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one, 2.5 g of potassium carbonate and 0.8 g of potassium iodide in 25 ml of N,N-dimethylformamide and 25 ml of toluene was stirred at 100° C. for 24 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 oxalic acid was added thereto to make oxalate. The resulting crystals were recrystallized from isopropyl alcohol to give 0.12 g of 7-(4-(4-(1,2-benzisothiazol-3-yl) piperazin-1-yl)butyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one oxalate 1/2 hydrate as white crystals, m.p. 118°-120° 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. additionoxalic acid was added
  9. customThe resulting crystals were recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-2dffb9b2d6bf4db5858884ef2c802975
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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