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

HRID 1193630Notes

Reaction equation

HRID 1193630 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 isopropyl 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-668494148b2e4cffa5945cdc0951dc55
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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