Potassium Iodide → HCID 19881143, compound

HRID 847391Notes

Reaction equation

HRID 847391 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[CH:15][S:16][C:10]=2[S:9](=[O:18])(=[O:17])[CH2:8][CH2:7]1.Cl.Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[N:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C1(C)C=CC=CC=1.CN(C)C=O>[N:21]1[CH:26]=[CH:25][CH:24]=[N:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:12](=[O:13])[C:11]3[CH:14]=[CH:15][S:16][C:10]=3[S:9](=[O:18])(=[O:17])[CH2:8][CH2:7]2)[CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 116802722-Piperazinylpyrimidine dihydrochlorideHCID 19881056HCID 19881056, compound

Product 1

HCID 19881143HCID 19881143, compoundYield 51.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4.1 g of 4-(4-chlorobutyl)-2,3-dihydrothieno[3,2-f]-1,4-thiazepin-5(4H)-one 1,1-dioxide in 80 ml of a mixed solvent of N,N-dimethylformamide and toluene (1:1) were added 3.2 g of N-(2-pyrimidinyl)piperazine dihydrochloride, 3.8 g of potassium carbonate and 2.3 g of potassium iodide and the mixture was stirred for 3 hours at 90° C. Then, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and the solvent was distilled off. The resulting residue was chromatographed on a silica gel and eluted using chloroform and methanol (95:5) as an eluent. The resulting crystals were recrystallized from ethanol to give 3.0 g of 2,3-dihydro-4-[4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl]thieno[3,2-f]-1,4-thiazepin-5(4H)-one 1,1-dioxide as white crystals, melting at 161°-163° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe resulting residue was chromatographed on a silica gel
  6. washeluted
  7. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-7be4b1e662664f65ac96f74a55046d83
Source dataset
uspto-grants-1992_08
Patent number
US05141930

Reaction notes

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