HCID 12298154, compound → 4-Piperidinecarboxylic acid, 4-[(3-methoxyphenyl)amino]-, methyl ester

HRID 1973804Notes

Reaction equation

HRID 1973804 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2([C:23]([O:25][CH3:26])=[O:24])[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1.[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10]2([C:23]([O:25][CH3:26])=[O:24])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 12298154HCID 12298154, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 122981734-Piperidinecarboxylic acid, 4-[(3-methoxyphenyl)amino]-, methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 60 parts of methyl 4-[N-(3-methoxyphenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylate and 400 parts of ethanol is hydrogenated at normal pressure and at room temperature with 10 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 residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 10% of methanol, previously saturated with gaseous ammonia, as eluent. The pure fractions are collected and the eluent is evaporated, yielding methyl 4-[N-(3-methoxyphenyl)amino]-4-piperidinecarboxylate as an oily residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is purified by column-chromatography over silica gel using
  4. additiona mixture of trichloromethane and 10% of methanol
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated

Sources & evidence

ORD record
ord-303ba88a098148aab14377f03007728a
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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