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 1734041Notes

Reaction equation

HRID 1734041 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 1.2 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. 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-093e99105bb54fa999738dc3e728ba65
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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