Nitromethane → HCID 14153812, compound

HRID 1252999Notes

Reaction equation

HRID 1252999 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Na].[CH3:6][N:7]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]1.[N+:14]([CH3:17])([O-])=O>C(O)C.C(O)(=O)C>[C:2]([O:13][C:10]1([CH2:17][NH2:14])[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]1)(=[O:1])[CH3:3]

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 740491-Methyl-4-piperidoneHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 14153812HCID 14153812, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of sodium ethoxide prepared by dissolving 23 g (1 mole) of sodium in 1500 ml of ethanol was added dropwise a mixture of 113 g (1 mole) of 1-methyl-4-piperidinone and 75 g (1.3 mole) of nitromethane at a rate so as to maintain a temperature (preheated) of 50° C. The solution was stirred for 4 hr and 150 g of acetic acid was added dropwise. The mixture was filtered and the filtrate was concentrated. The residue was crystallized from ethyl acetate. The resulting solid was dissolved in 1 liter of ethanol and treated with 2 teaspoonsful of Raney nickel catalyst. The mixture was hydrogenated for 3 hr at ambient temperature. The residue was crystallized from acetonitrile. Yield of title compound was 80 g (39%).

Workup

  1. additionwas added dropwise
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was crystallized from ethyl acetate
  5. dissolutionThe resulting solid was dissolved in 1 liter of ethanol
  6. additiontreated with 2 teaspoonsful of Raney nickel catalyst
  7. waitThe mixture was hydrogenated for 3 hr at ambient temperature
  8. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-0a70538820ed4b1c953799bd20a71a3d
Source dataset
uspto-grants-1988_05
Patent number
US04746655

Reaction notes

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