Ethyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoate → Ethyl 4-[(4-hydroxy-4-piperidinyl)methoxy]benzoate

HRID 1030912Notes

Reaction equation

HRID 1030912 reaction equation
[OH:1][C:2]1([CH2:15][O:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][N:5](CC2C=CC=CC=2)[CH2:4][CH2:3]1.[H][H]>[Pd].C(O)C>[OH:1][C:2]1([CH2:15][O:16][C:17]2[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14989213Ethyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 14989214Ethyl 4-[(4-hydroxy-4-piperidinyl)methoxy]benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 23 parts of ethyl 4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzoate and 200 parts of ethanol was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated, yielding 17 parts (100%) of ethyl 4-[(4-hydroxy-4-piperidinyl)methoxy]benzoate as a residue (int. 79).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-71d43e98d7ba41889540be443b1127b1
Source dataset
uspto-grants-1992_04
Patent number
US05106973

Reaction notes

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