Water → HCID 21108113, compound

HRID 1766023Notes

Reaction equation

HRID 1766023 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:30])[CH2:15][CH2:16][C:17]([C:19]3[CH:29]=[CH:28][C:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27][C:21]=4[CH:20]=3)=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.I[CH2:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:30])[CH2:15][CH2:16][C:17]([C:19]3[CH:29]=[CH:28][C:22]4[CH2:23][CH2:24][N:25]([CH2:32][CH3:33])[CH2:26][CH2:27][C:21]=4[CH:20]=3)=[O:18])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21108117HCID 21108117, compound

Product 1

HCID 21108113HCID 21108113, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-[4-(4-chlorophenyl)-1-piperidinyl]-4-oxo-1-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1-butanone (200 mg, 0.47 mmol) obtained in Example 15, iodoethane (0.0376 ml, 0.47 mmol) and potassium carbonate (138 mg, 1.0 mmol) in acetonitrile (5 ml) was stirred at room temperature for 12 hours, then poured into water and extracted with ethyl acetate. The extract was washed with a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the residues were purified by alumina silica gel column chromatography (developing solvent; ethyl acetate), whereby 101 mg of the title compound was obtained as colorless powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled away under reduced pressure
  5. customthe residues were purified by alumina silica gel column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-57472c521f984f3985c61d2b98e988ae
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

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