HCID 14698737, compound → HCID 11323901, compound

HRID 345470Notes

Reaction equation

HRID 345470 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[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(O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 14698737HCID 14698737, compound

Product 1

HCID 11323901HCID 11323901, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 38.5 g (0.1 mole) of α,α-bis(4-methylphenyl)-1-(phenylmethyl)-4-piperidinemethanol in 500 ml of absolute ethanol was hydrogenated at 50 psi and 60° C. over 1 tsp of 5% palladium on carbon in a Parr apparatus for 3 days. The cooled mixture was filtered through Celite® and the filtrate was concentrated under reduced pressure to give a glass as residue. The glass was crystallized from 2-propanol to yield 17.7 g (60%) of the title compound as a white solid, mp 150°-153° C.

Workup

  1. filtrationThe cooled mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a glass as residue
  4. customThe glass was crystallized from 2-propanol

Sources & evidence

ORD record
ord-e35c2c669057440d85366f7ad85b75b7
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

Loading…