HCID 70544672, compound → HCID 13192234, compound

HRID 1389849Notes

Reaction equation

HRID 1389849 reaction equation
[OH:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH2:3]1>CO.[Pd]>[OH:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 1

HCID 70544672HCID 70544672, compound

Product 1

HCID 13192234HCID 13192234, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8.2 g (0.025 mol) of trans-3-hydroxy-4-phenoxy-1-carbobenzyloxy-piperidine are dissolved in 140 ml of methanol and hydrogenated in the presence of 0.8 g of a 5% strength palladium-on-charcoal catalyst under normal pressure and at room temperature. After the absorption of hydrogen has ceased, the catalyst is filtered off by means of diatomaceous earth and the filtrate is evaporated under a water pump vacuum. The crude base crystallies from methanol/ether and gives trans-3-hydroxy-4-phenoxy-piperidine with a melting point of 134°-136°. The neutral fumarate prepared therefrom with fumaric acid crystallises from methanol/ether; melting point 180°-183°.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst is filtered off by means of diatomaceous earth
  3. customthe filtrate is evaporated under a water pump vacuum

Sources & evidence

ORD record
ord-ec1379b89cb9452e802645038d53ab63
Source dataset
uspto-grants-1981_01
Patent number
US04246269

Reaction notes

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