4,4-Difluoro-1′-(phenylmethyl)-1,4′-bipiperidine → 4,4-difluoro-1,4'-bipiperidine

HRID 644330Notes

Reaction equation

HRID 644330 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][C:17]([F:21])([F:20])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.Cl.[Pd]>[F:21][C:17]1([F:20])[CH2:18][CH2:19][N:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:15][CH2:16]1

Participants

6

Reactant 2

HCID 685813714,4-Difluoro-1′-(phenylmethyl)-1,4′-bipiperidineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 534187744,4-difluoro-1,4'-bipiperidine

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.8 g (9.5 mmol) 1′-benzyl-4,4-difluoro-[1,4′]bipiperidinyl in 300 mL MeOH was hydrogenated in the presence of 1.2 g Pd/C (10%) at 50° C. and 50 psi hydrogen pressure with the addition of a few drops of 1 M HCl until the calculated volume of hydrogen had been taken up. The catalyst was filtered off and the filtrate was evaporated down under reduced pressure. The residue was triturated with diisopropylether, suction filtered and dried.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down under reduced pressure
  3. customThe residue was triturated with diisopropylether, suction
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-b9641564546c46fb8ebb21f5e72aff44
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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