alpha,alpha-Diphenyl-1-(phenylmethyl)-4-piperidinemethanol → Azacyclonol

HRID 1709842Notes

Reaction equation

HRID 1709842 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH:9]2[CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11][CH2:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(O)C>[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 415512alpha,alpha-Diphenyl-1-(phenylmethyl)-4-piperidinemethanol

Product 1

HCID 15723AzacyclonolYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 35.8 g (0.1 mole) of α,α-diphenyl-1-(phenylmethyl)-4-piperidinemethanol and 5% palladium on carbon catalyst in 500 ml of absolute ethanol was hydrogenated at 60° C. in a Parr apparatus for 3 days. The mixture was filtered through Celite® and the filtrate was concentrated to give a solid residue. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration and dried to give 26.7 g of title compound as a white solid. An analytical sample was obtained by recrystallization from 2-propanol-isopropyl ether, mp 160°-161° C.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated
  3. customto give a solid residue
  4. customThe solid was triturated with petroleum ether (30°-60° C.)
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c640e4c8d58c46d193b41543a9a97e70
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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