Benzaldehyde → HCID 18383989, compound

HRID 1729472Notes

Reaction equation

HRID 1729472 reaction equation
[N+:1]([CH2:4][CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][C:7]([O:9]CC)=O)([O-:3])=[O:2].[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])(=O)C.[NH4+:30]>C(O)C>[C:12]1([CH:5]2[CH:4]([N+:1]([O-:3])=[O:2])[CH:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:30][C:7](=[O:9])[CH2:6]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 517165Ammonium AcetateHCID 11128315HCID 11128315, compound

Product 1

HCID 18383989HCID 18383989, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Under a nitrogen atmosphere in a round-bottom flask equipped with a reflux condenser were placed 21.1 g (89 mmol) of ethyl 4-nitro-3-phenylbutyrate (McMurray, J. E. et. al., Syn.Comm., 8, 53(1978)) and 90 mL of ethanol. To the system was added 9.04 mL (89 mmol) of benzaldehyde and 13.7 g (180 mmol) of ammonium acetate, and the reaction mixture was heated at 70° C. overnight. The reaction mixture was cooled, a small volume of ethanol was added and the suspension was filtered. The collected solid was rinsed with a small volume of ethanol followed by ether to afford 22.7 g of 4,6-diphenyl-5-nitro-2-oxopiperidine.

Workup

  1. customUnder a nitrogen atmosphere in a round-bottom flask equipped with a reflux condenser
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe suspension was filtered
  4. washThe collected solid was rinsed with a small volume of ethanol

Sources & evidence

ORD record
ord-f7ff9a2c79b3423ab6f6724291a0082f
Source dataset
uspto-grants-1994_07
Patent number
US05332817

Reaction notes

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