alpha,alpha-Bis(4-fluorophenyl)-4-pyridineethanol → alpha,alpha-Bis(4-fluorophenyl)-4-piperidineethanol

HRID 1460244Notes

Reaction equation

HRID 1460244 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)([OH:16])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1>[Pt].C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)([OH:16])[CH2:9][CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15020359alpha,alpha-Bis(4-fluorophenyl)-4-pyridineethanol

Product 1

HCID 13754513alpha,alpha-Bis(4-fluorophenyl)-4-piperidineethanolYield 85%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 12.25 g (0.0394 mole) of α,α-bis(4-fluorophenyl)-4-pyridineethanol and 1.3 g of 5% platinum on carbon catalyst in 250 ml of acetic acid was shaken under an atmosphere of hydrogen (53 psi) for 9 hr. The solution was filtered through Celite®, and the solvent was removed in vacuo. The residue was partitioned between methylene chloride and dilute sodium hydroxide. The solvent was removed in vacuo to give a solid. Recrystallization from acetonitrile gave 10.62 g (85% yield) of title compound as a white, crystalline solid, mp 169°-171° C.

Workup

  1. filtrationThe solution was filtered through Celite®
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between methylene chloride and dilute sodium hydroxide
  4. customThe solvent was removed in vacuo
  5. customto give a solid
  6. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-03df82e5ca78412b802d8e64b255b8a7
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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