Dichloromethane → Bis(4-fluorophenyl)(piperidin-4-yl)methanol

HRID 1709807Notes

Reaction equation

HRID 1709807 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)([CH:10]2[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.C(Cl)Cl>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)([CH:10]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]2)[OH:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 13519964alpha,alpha-Bis(4-fluorophenyl)-1-(phenylmethyl)-4-piperidinemethanol

Product 1

HCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 31.2 g (0.079 mole) of α,α-bis-(4-fluorophenyl)-1-(phenylmethyl)4-piperidinemethanol in 400 ml of absolute ethanol was hydrogenated at 50 psi and 70° C. over 5% palladium on carbon over the weekend. The mixture was filtered and the filtrate was concentrated under reduced pressure to give a gum as residue. Methylene chloride was added to the residue and the gum crystallized. The mixture was diluted with petroleum ether and the solid was collected by filtration, washed with petroleum ether, and dried to yield 22 g (92%) of white solid which was recrystallized from 2-propyl ether/2-propanol, m.p. 159.5°-160.5° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a gum as residue
  4. customthe gum crystallized
  5. additionThe mixture was diluted with petroleum ether
  6. filtrationthe solid was collected by filtration
  7. washwashed with petroleum ether
  8. customdried

Sources & evidence

ORD record
ord-ba268c9e01524379beb3cbecf5edfb06
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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