Potassium Iodide → HCID 21471901, compound

HRID 2294842Notes

Reaction equation

HRID 2294842 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[S:17][C:10]2[C:11](=[O:16])[NH:12][CH2:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:6].Cl.[F:19][C:20]1[CH:34]=[CH:33][C:23]2[C:24]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[N:25][O:26][C:22]=2[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[F:19][C:20]1[CH:34]=[CH:33][C:23]2[C:24]([CH:27]3[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH2:4][C:5]([C:7]4[S:17][C:10]5[C:11](=[O:16])[NH:12][CH2:13][CH2:14][CH2:15][C:9]=5[CH:8]=4)=[O:6])[CH2:31][CH2:32]3)=[N:25][O:26][C:22]=2[CH:21]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochlorideHCID 21471762HCID 21471762, compound

Product 1

HCID 21471901HCID 21471901, compoundYield 29.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.1 g of 2-(4-chlorobutyryl)-4,5,6,7-tetrahydro-8H-thieno[2,3-c]azepin-8-one, 1.1 g of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine hydrochloride, 1.68 g of potassium carbonate and 670 mg of potassium iodide in 10 ml of dimethylformamide and 10 ml of toluene was stirred at 90° C. for 22 hours and concentrated in vacuo. To the residue were added ethyl acetate and water, and separated. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on a silica gel and recrystallized from ethyl acetate-isopropyl ether to give 0.55 g of 2-(4-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)butyryl)-4,5,6,7-tetrahydro-8H-thieno[2,3-c]azepin-8-one 1/2hydrate, m.p. 186°-187° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue were added ethyl acetate and water
  3. customseparated
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on a silica gel
  8. customrecrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-5e8c84522fb24192bdb4492b09ec95e3
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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