Benzylamine → Ethyl cis-4-amino-3-ethoxy-1-piperidinecarboxylate

HRID 345555Notes

Reaction equation

HRID 345555 reaction equation
[CH2:1]([O:3][CH:4]1[C:9](=O)[CH2:8][CH2:7][N:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5]1)[CH3:2].C1(C[NH2:23])C=CC=CC=1.S1C=CC=C1.[H][H]>C(O)C.[Pd].CO>[NH2:23][C@H:9]1[CH2:8][CH2:7][N:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:5][C@H:4]1[O:3][CH2:1][CH3:2]

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8030ThiopheneHCID 15096763HCID 15096763, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67914569Ethyl cis-4-amino-3-ethoxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 21 parts of ethyl 3-ethoxy-4-oxo-1-piperidinecarboxylate, 11 parts of benzenemethanamine, 1 part of a solution of thiophene in ethanol 4% and 320 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, yielding 18 parts of ethyl cis-4-amino-3-ethoxy-1-piperidinecarboxylate as a residue (intermediate 69).

Workup

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

Sources & evidence

ORD record
ord-2e337c462f65432ba6029fa4865195c8
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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