Benzaldehyde → 58373-38-9

HRID 863772Notes

Reaction equation

HRID 863772 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)(=O)C.ClCCl>[N+:1]([CH:4]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:23][C:7](=[O:9])[CH2:6][CH2:5]1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 25604Methyl 4-nitrobutyrateHCID 517165Ammonium Acetate

Product 1

HCID 31722058373-38-9

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of methyl 4-nitrobutyrate (23g) and benzaldehyde (16ml) in acetic acid (39ml) containing ammonium acetate (12.12g) was heated at reflux under nitrogen for 2h. The reaction mixture was cooled to 5° C., whereby a pale-yellow solid crystallised. This was isolated by filtration, then dissolved in dichloromethane, washed cautiously with saturated aqueous sodium bicarbonate solution (2×), then dried (MgSO4) and concentrated to leave a yellow solid. Recrystallisation from ethyl acetate provided 5-nitro-2-oxo-6-phenylpiperidine (12.5g) as a crystalline, white solid. 1H NMR (CDCl3) δ7.46-7.26 (m), 6.0 (br s), 5.24 (dd, J=1.4, 7.0Hz), 4.70 (m), 2.70-2.50 (m), 2.38-2.24 (m).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 2h
  3. customwhereby a pale-yellow solid crystallised
  4. customThis was isolated by filtration
  5. washwashed cautiously with saturated aqueous sodium bicarbonate solution (2×)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto leave a yellow solid
  9. customRecrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-b4caab8158914b1cb88aeced52221c4c
Source dataset
uspto-grants-1996_10
Patent number
US05561130

Reaction notes

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