Ammonia → Methyl 4-[(ethoxycarbonyl)phenylamino]-4-piperidinecarboxylate

HRID 1448338Notes

Reaction equation

HRID 1448338 reaction equation
[CH2:1]([O:3][C:4]([N:6]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:7]1([C:23]([O:25][CH3:26])=[O:24])[CH2:12][CH2:11][N:10](C(OCC2C=CC=CC=2)=O)[CH2:9][CH2:8]1)=[O:5])[CH3:2].N.[H][H]>[Pd].CO>[CH2:1]([O:3][C:4]([N:6]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:7]1([C:23]([O:25][CH3:26])=[O:24])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 86734315O4-methyl O1-(phenylmethyl) 4-[(ethoxycarbonyl)phenylamino]-1,4-piperidinedicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 54241043Methyl 4-[(ethoxycarbonyl)phenylamino]-4-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

A solution of 16.2 parts of O4 -methyl O1 -(phenylmethyl) 4-[(ethoxycarbonyl)phenylamino]-1,4-piperidinedicarboxylate in 200 parts of methanol and 20 parts of methanol, previously saturated with ammonia is hydrogenated at normal pressure and at room temperature with 3 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, yielding 11.7 parts of methyl 4-[(ethoxycarbonyl)phenylamino]-4-piperidinecarboxylate as an oily residue.

Workup

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

Sources & evidence

ORD record
ord-4314b4c067954139ab6cfeee467bf76c
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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