Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylate → Ethyl 5-amino-1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate

HRID 1593596Notes

Reaction equation

HRID 1593596 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:24]>CO>[CH2:17]([O:16][C:14]([C:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][C:10]=1[NH2:24])=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 419705Ethyl 3-oxo-1-(phenylmethyl)-4-piperidinecarboxylateHCID 517165Ammonium Acetate

Product 1

HCID 51358389Ethyl 5-amino-1-benzyl-1,2,3,6-tetrahydropyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate (25 g, 83.96 mM) and ammonium acetate (32.36 g, 419.79 mM) in MeOH (250 mL) were agitated overnight. The mixture was concentrated, the crude product was dissolved in methylene chloride and washed sequentially with aqueous saturated potassium carbonate solution and water. The organic was dried and reduced in vacuo to yield the title compound (24.0 g, 110%, higher yield possibly due to accluded solvents) as an oil which solidified on standing.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe crude product was dissolved in methylene chloride
  3. washwashed sequentially with aqueous saturated potassium carbonate solution and water
  4. customThe organic was dried

Sources & evidence

ORD record
ord-bd776a7c34bb4c058fd0ba8ac4110e95
Source dataset
uspto-grants-2007_11
Patent number
US07297700B2

Reaction notes

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