Methanol → HCID 54545632, compound

HRID 1872763Notes

Reaction equation

HRID 1872763 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:3]1.[CH2:20]([NH2:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CO>S1C=CC=C1.[Pd]>[C:14]1([CH2:13][CH:4]2[CH2:3][CH:2]([NH:27][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:7][CH2:6][N:5]2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 7504BenzylamineHCID 54513616HCID 54513616, compound

Product 1

HCID 54545632HCID 54545632, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8030ThiopheneSolvent

Procedure

A mixture of (±)-ethyl 4-oxo-2-(phenylmethyl)-1-piperidinecarboxylate (10 g) and benzylamine (4 g) was hydrogenated at 50° C. in thiophene (4% solution; 1 ml) and methanol (150 ml) with palladium on activated carbon (10%; 3 g) as a catalyst. After uptake of hydrogen, the catalyst was filtered off and the solvent was evaporated, yielding (±)-ethyl 2-(phenylmethyl)-4-[(phenylmethyl)amino]-1-piperidine-carboxylate (interm. 22).

Workup

  1. filtrationAfter uptake of hydrogen, the catalyst was filtered off
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4cad1d1e07ad4a6eb96fa1b68265e8ca
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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