trans-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-4-[(phenylmethyl)amino]-1-piperidinebutanamide → trans-4-amino-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide

HRID 981307Notes

Reaction equation

HRID 981307 reaction equation
[OH:1][C@H:2]1[C@H:7]([NH:8]CC2C=CC=CC=2)[CH2:6][CH2:5][N:4]([CH:16]([CH3:36])[CH2:17][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:3]1.[H][H]>[Pd].COCCO>[NH2:8][C@@H:7]1[CH2:6][CH2:5][N:4]([CH:16]([CH3:36])[CH2:17][C:18]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:19]([N:21]([CH3:23])[CH3:22])=[O:20])[CH2:3][C@H:2]1[OH:1]

Participants

5

Reactant 2

HCID 67928753trans-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-4-[(phenylmethyl)amino]-1-piperidinebutanamideHCID 178418361HCID 178418361, compound

Product 1

HCID 67928771trans-4-amino-3-hydroxy-N,N,gamma-trimethyl-alpha,alpha-diphenyl-1-piperidinebutanamideYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 63 parts of trans-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-4-[(phenylmethyl)amino]-1-piperidinebutanamide and 485 parts of 2-methoxyethanol was hydrogenated at normal pressure and at 50° C. with 5 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 with methylbenzene, yielding 45 parts (87.5%) of trans-4-amino-3-hydroxy-N,N,γ-trimethyl-α,α-diphenyl-1-piperidinebutanamide (interm. 9).

Workup

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

Sources & evidence

ORD record
ord-208223eb5f0f4b9f951a0cd4a737dbd6
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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