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Potassium Iodide → HCID 86749602, compound

HRID 1734073
Notes
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Reaction equation

HRID 1734073 reaction equation
C([N:4]1[CH2:10][CH2:9][CH2:8][C:7]2[CH:11]=[C:12]([C:14](=[O:19])[CH2:15][CH2:16][CH2:17]Cl)[S:13][C:6]=2[CH2:5]1)(=O)C.Cl.[F:21][C:22]1[CH:36]=[CH:35][C:25]2[C:26]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[N:27][O:28][C:24]=2[CH:23]=1.[C:37](=[O:40])([O-])[O-].[K+].[K+].[I-].[K+].[CH3:45]N(C)C=O>C1(C)C=CC=CC=1>[C:37]([C:11]1[C:7]2[CH2:8][CH2:9][CH2:10][NH:4][CH2:5][C:6]=2[S:13][C:12]=1[C:14](=[O:19])[CH2:15][CH2:16][CH2:17][N:32]1[CH2:31][CH2:30][CH:29]([C:26]2[C:25]3[CH:35]=[CH:36][C:22]([F:21])=[CH:23][C:24]=3[O:28][N:27]=2)[CH2:34][CH2:33]1)(=[O:40])[CH3:45]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11334359R-56109 hydrochlorideHCID 21471818HCID 21471818, compound

Product 1

HCID 86749602HCID 86749602, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.8 g of 7-acetyl-2-(4-chlorobutyryl)-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine, 2.6 g of 4-(6-fluoro-1,2-benzisoxazol- 3-yl)piperidine hydrochloride, 3.9 g of potassium carbonate and 1.55 g of potassium iodide in 30 ml of dimethylformamide and 30 ml of toluene was stirred at 70° C. for 20 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 to give 3.0 g of 7-(acetyl-2-(4-(4-(6-fluoro-l,2-benzisoxazol-3-yl)piperidin-1-yl)butyryl)-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine as an oil. The oil was treated with hydrochloric acid in isopropyl alcohol and recrystallized from ethanol-ethyl acetate to give 7-acetyl-2-(4-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)butyryl)-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepine hydrochloride, m.p. 230° C. (decomposition).

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

Sources & evidence

ORD record
ord-46f324ede31f4ed6a603f7215128eb64
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05532240

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes