Ethylenediamine → methyl 3,6-dihydro-3-methyl-4-(nitromethyl)-1(2H)-pyridinecarboxylate

HRID 1761474Notes

Reaction equation

HRID 1761474 reaction equation
[CH3:1][CH:2]1[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3]1.C(N)CN.[N+:17]([CH3:20])([O-:19])=[O:18]>>[CH3:1][CH:2]1[C:7]([CH2:20][N+:17]([O-:19])=[O:18])=[CH:6][CH2:5][N:4]([C:9]([O:11][CH3:12])=[O:10])[CH2:3]1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 6375NitromethaneHCID 3015586Methyl 3-methyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 21241597methyl 3,6-dihydro-3-methyl-4-(nitromethyl)-1(2H)-pyridinecarboxylateYield 87.2%

Procedure

A mixture of 64 parts of methyl 3-methyl-4-oxo-1-piperidinecarboxylate, 305 parts of nitromethane and 3.02 parts of 1,2-ethanediamine was stirred and refluxed for 4 hours. The reaction mixture was evaporated. The residue was taken up in trichloromethane. The solution was washed twice with a dilute hydrochloric acid solution, dried, filtered and evaporated, yielding 70 parts (87.2%) of methyl 3,6-dihydro-3-methyl-4-(nitromethyl)-1-(2H)-pyridinecarboxylate as a residue (intermediate 1).

Workup

  1. temperaturerefluxed for 4 hours
  2. customThe reaction mixture was evaporated
  3. washThe solution was washed twice with a dilute hydrochloric acid solution
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e03278c8c61a472f8eabab6393af2602
Source dataset
uspto-grants-1989_05
Patent number
US04826848

Reaction notes

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