HCID 15020351, compound → HCID 15020352, compound

HRID 1460232Notes

Reaction equation

HRID 1460232 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)([CH:10]2[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12][CH2:11]2)[OH:9])[CH:5]=[CH:6][CH:7]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15020351HCID 15020351, compound

Product 1

HCID 15020352HCID 15020352, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 39.3 g (0.1 mole) of α,α-bis(3-fluorophenyl)-1-(phenylmethyl)-4-piperidinemethanol in 750 ml of absolute ethanol was hydrogenated over palladium on carbon in a Parr apparatus at 50 psi and 60° C. for 3.5 days. The mixture was cooled and filtered through Celite®. The filtrate was concentrated, and the residue was dissolved in ethyl ether and filtered through cotton to remove some insoluble material. The filtrate was concentrated to give a gum which crystallized when triturated with petroleum ether (30°-60° C.). The solid was collected by filtration and dried to yield 27.9 g (92%) of the title compound as a white solid. An analytical sample, mp 117°-118° C., was recrystallized from isopropyl ether/2-propanol.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in ethyl ether
  5. filtrationfiltered through cotton
  6. customto remove some insoluble material
  7. concentrationThe filtrate was concentrated
  8. customto give a gum which
  9. customcrystallized when
  10. customtriturated with petroleum ether (30°-60° C.)
  11. filtrationThe solid was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-b19b085ab827452c86c2360b082259e3
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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