Ammonia → HCID 11437128, compound

HRID 361402Notes

Reaction equation

HRID 361402 reaction equation
C[N:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([N+]([O-])=O)[C:3]1=O.[CH2:15]([N:22]1[CH2:27]CC(=O)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N>CO>[CH2:15]([N:22]1[CH2:23][CH2:24][C:3]2[N:2]=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=2[CH2:27]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 192201-Benzyl-4-piperidoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 11437128HCID 11437128, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-methyl-3,5-dinitro-2-pyridone (1.2 g, 6.0 mmol), 1-benzyl-4-piperidone (1.12 g, 5.9 mmol) and ammonia solution in methanol (2.0M, 60 mL) was refluxed for 3 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate. The soluble portion was flash chromatographed over silica gel (eluent: 90:1 v/v ethyl acetate-hexane) to give a yellow solid (0.79 g, 49.7% yield).

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customchromatographed over silica gel (eluent: 90:1 v/v ethyl acetate-hexane)

Sources & evidence

ORD record
ord-de0c28b668dc465eb582067e2389b00d
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Reaction notes

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