Methyl 3-methyl-4-[(phenylmethyl)amino]-1-piperidinecarboxylate → Methyl 4-amino-3-methylpiperidine-1-carboxylate

HRID 2248796Notes

Reaction equation

HRID 2248796 reaction equation
[CH3:1][CH:2]1[CH:7]([NH:8]CC2C=CC=CC=2)[CH2:6][CH2:5][N:4]([C:16]([O:18][CH3:19])=[O:17])[CH2:3]1.[H][H]>[Pd].CO>[NH2:8][CH:7]1[CH2:6][CH2:5][N:4]([C:16]([O:18][CH3:19])=[O:17])[CH2:3][CH:2]1[CH3:1]

Participants

5

Reactant 2

HCID 19785254Methyl 3-methyl-4-[(phenylmethyl)amino]-1-piperidinecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19785295Methyl 4-amino-3-methylpiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 40 parts of methyl 3-methyl-4-[(phenylmethyl)amino]-1-piperidinecarboxylate and 160 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 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 to dry. The residue was distilled (bp. 80° C. at 0.1 mm. pressure). The distillate was further purified by gas-chromatography (at 215° C. and at 10 lbs/sq. inch), yielding 8.6 parts of methyl 4-amino-3-methyl-1-piperidinecarboxylate (interm. 27)

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customto dry
  4. distillationThe residue was distilled (bp. 80° C. at 0.1 mm. pressure)
  5. distillationThe distillate was further purified by gas-chromatography (at 215° C. and at 10 lbs/sq. inch)

Sources & evidence

ORD record
ord-b634badc0828420e89e1f1d436b841b9
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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