HCID 12298160, compound → 4-Piperidinecarboxylic acid, 4-[(4-fluorophenyl)amino]-, methyl ester

HRID 1973807Notes

Reaction equation

HRID 1973807 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:22]([O:24][CH3:25])=[O:23])[CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:22]([O:24][CH3:25])=[O:23])[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12298160HCID 12298160, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 122981784-Piperidinecarboxylic acid, 4-[(4-fluorophenyl)amino]-, methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 53 parts of methyl 4-[(4-fluorophenyl)amino]-1-(phenylmethyl)-4-piperidinecarboxylate and 400 parts of methanol is hydrogenated at normal pressure and at room temperature with 10 parts of palladium-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 15% of methanol, previously saturated with gaseous ammonia, as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue solidifies on scratching in hexane. The product is filtered off and dried, yielding methyl 4-[(4-fluorophenyl)amino]-4-piperidinecarboxylate; mp. 83.7° C.

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 15% of methanol
  5. customThe pure fractions are collected
  6. customthe eluent is evaporated
  7. filtrationThe product is filtered off
  8. customdried

Sources & evidence

ORD record
ord-58cb91c175e2425e847317b5fe557ca9
Source dataset
uspto-grants-1976_12
Patent number
US03998834

Reaction notes

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