Benzylamine → 1-Piperidinecarboxylic acid, 3-(phenylmethoxy)-4-[(phenylmethyl)amino]-, ethyl ester, cis-

HRID 846743Notes

Reaction equation

HRID 846743 reaction equation
S1C=CC=C1.O=[C:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH:8]1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:26]1([CH2:32][NH2:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[H][H]>[Pd].CO.C(O)C>[C:20]1([CH2:19][O:18][C@H:8]2[C@@H:7]([NH:33][CH2:32][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:12][CH2:11][N:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8030ThiopheneHCID 3019711Ethyl 3-(benzyloxy)-4-oxopiperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 136777451-Piperidinecarboxylic acid, 3-(phenylmethoxy)-4-[(phenylmethyl)amino]-, ethyl ester, cis-

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 5 parts of a solution of 2 parts of thiophene in 40 parts of ethanol, were added 135 parts of ethyl 4-oxo-3-(phenylmethoxy)-1-piperidinecarboxylate, 55 parts of benzenemethanamine and 400 parts of methanol. The whole was hydrogenated at normal pressure and at 50° C. with 8 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 170 parts of ethyl cis-3-(phenylmethoxy)-4-[(phenylmethyl)amino]-1-piperidinecarboxylate as an oily residue (intermediate 48).

Workup

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

Sources & evidence

ORD record
ord-67532aed5b904f52b4684dcca3160e44
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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