Methyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylate → 4-Piperidinecarboxylic acid, 4-(phenylamino)-, methyl ester

HRID 1973834Notes

Reaction equation

HRID 1973834 reaction equation
[C:1]1([NH:7][C:8]2([C:21]([O:23][CH3:24])=[O:22])[CH2:13][CH2:12][N:11](CC3C=CC=CC=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>[Pd].CO>[C:1]1([NH:7][C:8]2([C:21]([O:23][CH3:24])=[O:22])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 2724430Methyl 1-benzyl-4-(phenylamino)piperidine-4-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 122981714-Piperidinecarboxylic acid, 4-(phenylamino)-, methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 32.5 parts of methyl 4-(phenylamino)-1-(phenylmethyl)-4-piperidinecarboxylate and 200 parts of methanol is hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The oily residue solidifies on scratching in 2,2'-oxybispropane. The product is filtered off and dried in vacuo, yielding 20 parts (85%) of methyl 4-(phenylamino)-4-piperidinecarboxylate; mp. 139.1° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. filtrationThe product is filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-255c87924a99435184feb7000ca4356b
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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