Ethyl 3-(2-nitrobenzyl)-2-oxo-1-propyl-3-piperidinecarboxylate → HCID 18332960, compound

HRID 2269722Notes

Reaction equation

HRID 2269722 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][C:7]1([C:17](OCC)=[O:18])[CH2:12][CH2:11][CH2:10][N:9]([CH2:13][CH2:14][CH3:15])[C:8]1=[O:16])([O-])=O>[C].[Pd].C(O)C>[O:16]=[C:8]1[C:7]2([CH2:6][C:5]3[C:4](=[CH:25][CH:24]=[CH:23][CH:22]=3)[NH:1][C:17]2=[O:18])[CH2:12][CH2:11][CH2:10][N:9]1[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 1

HCID 18332952Ethyl 3-(2-nitrobenzyl)-2-oxo-1-propyl-3-piperidinecarboxylate

Product 1

HCID 18332960HCID 18332960, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% Palladium- carbon (0.2 g) was added to an ethanol solution (20 ml) of ethyl 3-(2-nitrobenzyl)-2-oxo-1-propyl-3-piperidinecarboxylate (1.00 g), and catalytic hydrogenation was conducted at room temperature under one atmospheric pressure for 6 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was dissolved in toluene (20 ml), which was heated under reflux for 12 hours. The reaction mixture was concentrated, and the obtained crude crystals were recrystallized from ethyl acetate-hexane to give the entitled compound (0.55 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in toluene (20 ml)
  4. temperaturewhich was heated
  5. temperatureunder reflux for 12 hours
  6. concentrationThe reaction mixture was concentrated
  7. customthe obtained crude crystals
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-588de430343d40ec81df83959d8b1201
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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