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

HRID 345469Notes

Reaction equation

HRID 345469 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.CC(O)C.C(OC(C)C)(C)C>C(O)C.[Pd]>[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

5

Reactant 2

HCID 415512alpha,alpha-Diphenyl-1-(phenylmethyl)-4-piperidinemethanolHCID 21202047Isopropyl alcohol isopropyl ether

Product 1

HCID 15723Azacyclonol

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 1 tsp of 5% Pd/C 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 (quantitative) of white solid. An analytical sample, mp 160°-161° C., was prepared from 2-propanol-isopropyl ether.

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
  7. customto give 26.7 g (quantitative) of white solid

Sources & evidence

ORD record
ord-9b5b60513f574963a813168b186fe7fb
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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