Potassium Iodide → HCID 21471809, compound

HRID 1734065Notes

Reaction equation

HRID 1734065 reaction equation
Cl[CH2:2][CH2:3][C:4]1[S:14][C:7]2[C:8](=[O:13])[NH:9][CH2:10][CH2:11][CH2:12][C:6]=2[CH:5]=1.Cl.[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][C:4]4[S:14][C:7]5[C:8](=[O:13])[NH:9][CH2:10][CH2:11][CH2:12][C:6]=5[CH:5]=4)[CH2:28][CH2:29]3)=[N:22][O:23][C:19]=2[CH:18]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochlorideHCID 21471776HCID 21471776, compound

Product 1

HCID 21471809HCID 21471809, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 800 mg of 2-chloroethyl-4,5,6,7-tetrahydro-8H-thieno[2,3-c]azepin-8-one, 920 mg of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine hydrochloride, 1.45 g of potassium carbonate and 580 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 to give 0.65 g of 2-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)ethyl)-4,5,6,7-tetrahydro-8H-thieno[2,3-c]azepin-8-one, m.p. 192°-194° 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

Sources & evidence

ORD record
ord-3e4ada6686bf4b628577df51e306f713
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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