Potassium Iodide → 4-(4-Chlorophenyl)-1-[4-(3-methoxyphenyl)-4-(3-pyridinyl)-3-butenyl]piperidin-4-ol

HRID 1595227Notes

Reaction equation

HRID 1595227 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([OH:33])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([OH:33])[CH2:28][CH2:29][N:30]([CH2:2][CH2:3][CH:4]=[C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=3)[C:6]3[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=3)[CH2:31][CH2:32]2)=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 538732124-Bromo-1-(3-methoxyphenyl)-1-(3-pyridinyl)-1-butene

Product 1

HCID 571931264-(4-Chlorophenyl)-1-[4-(3-methoxyphenyl)-4-(3-pyridinyl)-3-butenyl]piperidin-4-ol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution the product of step 2 (500 mg) in DMF (20 ml) were added 4-(4-chlorophenyl)-4-hydroxypiperidine (50 mg), potassium carbonate (430 mg), potasium iodide (130 mg) and the mixture was stirred at room temperature for 12 hours. Water and ethyl acetate were added to the reaction mixture, the organic layer was separated and washed with saturated aqueous sodium chloride, and dried with magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with methylene chloride-methanol (10:1) to give the titled compound as major regioisomer (225 mg) and minor one (140 mg).

Workup

  1. customthe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with methylene chloride-methanol (10:1)

Sources & evidence

ORD record
ord-6bb704ecd36645adb677e42287df6315
Source dataset
uspto-grants-2001_09
Patent number
US06288084B1

Reaction notes

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