HCID 67462245, compound → HCID 67464241, compound

HRID 537211Notes

Reaction equation

HRID 537211 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[C:12]([C:16]2([F:37])[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)[CH:13]=[CH:14][CH:15]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[ClH:1].[C:31]1([CH:24]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:23][CH2:22][N:19]2[CH2:18][CH2:17][C:16]([F:37])([C:12]3[CH:13]=[CH:14][CH:15]=[C:10]([OH:9])[CH:11]=3)[CH2:21][CH2:20]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 67462245HCID 67462245, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67464241HCID 67464241, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(3-benzyloxyphenyl)-1-(3,3-diphenyl-propyl)-4-fluoropiperidine hydrochloride (40 mg, 0.08 mmol) in methanol (5 mL) was treated with palladium on carbon (10 mg, 10% Pd, 50% H2O) and the mixture rapidly stirred under 1 atmosphere of hydrogen gas for 8 hours. After this time the hydrogen was replaced by nitrogen and the reaction mixture filtered through a celite pad. The pad was washed with additional methanol (10 mL) and the filtrate concentrated under reduced pressure. Trituration of the residue with a 1:1 mixture of 2-butanone/ethyl acetate (10 mL) and subsequent filtration and drying afforded a 64% yield of 1-(3,3-diphenylpropyl)-4-fluoro-4-(3-hydroxyphenyl)piperidine hydrochloride as an off-white solid.

Workup

  1. filtrationthe reaction mixture filtered through a celite pad
  2. washThe pad was washed with additional methanol (10 mL)
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionTrituration of the residue with a 1:1 mixture of 2-butanone/ethyl acetate (10 mL) and subsequent filtration
  5. customdrying

Sources & evidence

ORD record
ord-7e27b5ef1c2e4a2cae63ea07a6904716
Source dataset
uspto-grants-2014_10
Patent number
US08859777B2

Reaction notes

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