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

HRID 2248795Notes

Reaction equation

HRID 2248795 reaction equation
[CH3:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3]1.[C:13]1([CH2:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.S1C=CC=C1.[H][H]>C(O)C.[Pd].CO>[CH3:1][CH:2]1[CH:7]([NH:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3]1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8030ThiopheneHCID 3015586Methyl 3-methyl-4-oxopiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19785254Methyl 3-methyl-4-[(phenylmethyl)amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 26 parts of methyl 3-methyl-4-oxo-1-piperidinecarboxylate, 16.5 parts of benzenemethanamine, 2 parts of a solution of thiophene in ethanol 4% and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 3 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, yielding 40.2 parts of methyl 3-methyl-4-[(phenylmethyl)amino]-1-piperidinecarboxylate as a residue (interm. 26).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customto dry

Sources & evidence

ORD record
ord-60772a1c2ec74ad4add8f86192d94ffc
Source dataset
uspto-grants-1991_08
Patent number
US05041448

Reaction notes

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