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

HRID 476925Notes

Reaction equation

HRID 476925 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 99%

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 (99%) of white solid which was recrystallized from isopropyl ether and 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-5662776341d944e69147cb51d8e88dbc
Source dataset
uspto-grants-1989_12
Patent number
US04886794

Reaction notes

Loading…