Benzaldehyde → HCID 1417894, compound

HRID 1781292Notes

Reaction equation

HRID 1781292 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=O)([O-:3])=[O:2].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[NH4+:23]>C(O)C>[N+:1]([C@@H:4]1[CH2:5][CH2:6][C:7](=[O:9])[NH:23][C@H:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 25604Methyl 4-nitrobutyrateHCID 517165Ammonium Acetate

Product 1

HCID 1417894HCID 1417894, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-nitrobutyrate (1) (240 g, 1.63 mol), benzaldehyde (189 g, 1.78 mol), ammonium acetate (164 g, 2.12 mol) and ethanol (1680 ml) were placed in a 3-liter 3-necked flask equipped with a mechanical stirrer, under an atmosphere of nitrogen. The mixture was heated under reflux for four hours to yield an orange solution which crystallised on cooling. The crystalline product was isolated by filtration, washed with ethanol, ether and then dried under vacuum to afford trans-3nitro-6-oxo-2-phenylpiperidine 304 g (85%): m.p. 174°-175° C.; 1H NMR (360 MHz, CDCl3) δ2.28-2.38 (1H, m; CHH), 2.51-2.71 (3H, m, CH2 +CHH), 4.69-4.74 (1H, m, CHNO2), 5.25 (1H, d, J=6.0 Hz, PhCHN), 6.0 (1H, brs, NH), 7.31-7.35 (2H, m, ArH), 7.38-7.45 (3H, m, ArH); 13C NMR (CDCl3 /DMSO), 22.92 (CH2), 27.62 (CH2), 58.58 (PhCHN), 85.01 (CNO2), 126.47 (Ar), 129.02 (Ar), 129.17 (Ar), 137.85 (Ar), 169.55 (C=O); Calculated for C11H12N2O3 ; C, 59.99; H, 5.49; N, 12.72. Found: C, 60.07; H, 5.60; N, 12.76%.

Workup

  1. customequipped with a mechanical stirrer, under an atmosphere of nitrogen
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for four hours
  4. customto yield an orange solution which
  5. customcrystallised
  6. temperatureon cooling
  7. customThe crystalline product was isolated by filtration
  8. washwashed with ethanol, ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-1c6e0a0c6762481f8f0b8e21fe0e5b9e
Source dataset
uspto-grants-1997_05
Patent number
US05633266

Reaction notes

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