HCID 13192226, compound → HCID 13192228, compound

HRID 1389844Notes

Reaction equation

HRID 1389844 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[CH2:9][CH2:8][N:7](C(OCC2C=CC=CC=2)=O)[CH2:6]1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13192226HCID 13192226, compound

Product 1

HCID 13192228HCID 13192228, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

16.0 g (0.04 mol) of trans-3-acetoxy-4-(3,4-dimethylphenoxy)-1-carbobenzyloxy-piperidine are dissolved in 400 ml of methanol and hydrogenated in the presence of 1.5 g of a 5% strength palladium-on-charcoal catalyst under normal pressure. After the reaction has ended, the catalyst is filtered off by means of a layer of diatomaceous earth and the filtrate is evaporated under a water pump vacuum, whereupon trans-3-acetoxy-4-(3,4-dimethylphenoxy)-piperidine is obtained in the form of a yellow oil. Reaction of the base with fumaric acid in ethanol/ether gives the crystalline acid fumarate with a melting point of 170°-172°.

Workup

  1. filtrationthe catalyst is filtered off by means of a layer of diatomaceous earth
  2. customthe filtrate is evaporated under a water pump vacuum

Sources & evidence

ORD record
ord-53eb276fa2db4c23a0cf8a57dadc8315
Source dataset
uspto-grants-1981_01
Patent number
US04246269

Reaction notes

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