N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamide → N-(2-hydroxyethyl)-4-[(4-hydroxy-4-piperidinyl)methoxy]benzamide

HRID 484498Notes

Reaction equation

HRID 484498 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:28])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2([OH:27])[CH2:19][CH2:18][N:17](CC3C=CC=CC=3)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.[H][H]>[Pd].CO>[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:28])[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][C:14]2([OH:27])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 14989215N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 19820922N-(2-hydroxyethyl)-4-[(4-hydroxy-4-piperidinyl)methoxy]benzamideYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 23 parts of N-(2-hydroxyethyl)-4-[[4-hydroxy-1-(phenylmethyl)-4-piperidinyl]methoxy]benzamide and 200 parts of methanol 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 16 parts (90.5%) of N-(2-hydroxyethyl)-4-[(4-hydroxy-4-piperidinyl) methoxy]benzamide as an oily residue (int. 81).

Workup

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

Sources & evidence

ORD record
ord-db3aaf5907d049209f7c1c541887066c
Source dataset
uspto-grants-1993_07
Patent number
US05231184

Reaction notes

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