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

HRID 2294812Notes

Reaction equation

HRID 2294812 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][C:26]([C:28]1[S:37][C:36]2[S:35][CH2:34][CH2:33][NH:32][C:31](=[O:38])[C:30]=2[CH:29]=1)=[O:27].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1.O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:9]2[CH2:10][CH2:11][N:12]([CH2:23][CH2:24][CH2:25][C:26]([C:28]3[S:37][C:36]4[S:35][CH2:34][CH2:33][NH:32][C:31](=[O:38])[C:30]=4[CH:29]=3)=[O:27])[CH2:13][CH2:14]2)=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2855101-[Bis(4-chlorophenyl)methyl]piperazineHCID 214720567-(4-chlorobutyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one

Product 1

HCID 214719787-(4-(4-(bis(4-chlorophenyl)-methyl)piperazin-1-yl)butyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-oneYield 4.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 2.4 g of 4-(bis(4-chlorophenyl)methyl)piperazine, 2.0 g of 7-(4-chlorobutyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one, 1.9 g of potassium carbonate and 1.2g 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. The precipitated crystals were filtered off and the filtrate was extracted with toluene. 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 and the resulting crystals were recrystallized from isopropyl alcohol-isopropyl ether to give 0.18 g of 7-(4-(4-(bis(4-chlorophenyl)-methyl)piperazin-1-yl)butyryl)-2,3-dihydrothieno[3,2-f][1,4]thiazepin-5(4H)-one as white crystals, m.p. 185°-187° C. (decomposition).

Workup

  1. temperatureAfter the mixture was cooled in a water bath
  2. filtrationThe precipitated crystals were filtered off
  3. extractionthe filtrate was extracted with toluene
  4. washThe organic layer was washed with saline solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on a silica gel
  8. customthe resulting crystals were recrystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-56dd226482c046bb8494e4760a93b469
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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