Benzylamine → Ethyl cis-(4-amino-3-methoxypiperidino)formate

HRID 345545Notes

Reaction equation

HRID 345545 reaction equation
S1C=CC=C1.[CH3:6][O:7][CH:8]1[C:13](=O)[CH2:12][CH2:11][N:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1.C1(C[NH2:27])C=CC=CC=1.[H][H]>[Pd].CO.C(O)C>[NH2:27][C@H:13]1[CH2:12][CH2:11][N:10]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][C@H:8]1[O:7][CH3:6]

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8030ThiopheneHCID 2724451Ethyl 3-methoxy-4-oxopiperidine-1-carboxylateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13677746Ethyl cis-(4-amino-3-methoxypiperidino)formate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 2 parts of a solution of 2 parts of thiophene in 40 parts of ethanol were added 126 parts of ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate, 70 parts of benzenemethanamine and 400 parts of methanol. The whole was hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After up-take of one equivalent of hydrogen, the catalyst was filtered off and hydrogenation was continued with another 5 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. The residue contained some oil drops which were separated, yielding 92.9 parts of ethyl cis-4-amino-3-methoxy-1-piperidinecarboxylate (intermediate 54).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customwere separated

Sources & evidence

ORD record
ord-36ede86238894873bb4a4ee426bb7f3b
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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