Nitromethane → 2-Nitromethylene-piperidine

HRID 2398727

Reaction equation

HRID 2398727 reaction equation
CO[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]=1.[N+:9]([CH3:12])([O-:11])=[O:10]>>[N+:9]([CH:12]=[C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4]1)([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 6375NitromethaneHCID 138567o-Methylvalerolactim

Product 1

HCID 7685842-Nitromethylene-piperidine

Procedure

A solution of 33.9 g of (1A) and 36.6 g of nitromethane was refluxed for 3 days, cooled and quenched in one liter of cold ether. Filtration gave a solid crude product, m.p. 79° - 81°. Evaporation of the filtrate and trituration of the residue with cold ether give additional crude product. The crude product was continuously extracted from a Soxhlet thimble with ether for 18 hours, after which time only a small amount of dark oil remained. The solvent pot (not containing crystallized product) was cooled and the solid product was filtered, giving 2-(nitromethylene)piperidine (1B), as a pale yellow solid, m.p.: 80.5°-81°.

Workup

  1. temperaturecooled
  2. customquenched in one liter of cold ether
  3. filtrationFiltration
  4. customgave a solid crude product, m.p. 79° - 81°
  5. customEvaporation of the filtrate and trituration of the residue with cold ether
  6. customgive additional crude product
  7. extractionThe crude product was continuously extracted from a Soxhlet thimble with ether for 18 hours
  8. additionThe solvent pot (not containing
  9. customcrystallized product)
  10. temperaturewas cooled
  11. filtrationthe solid product was filtered

Sources & evidence

ORD record
ord-894727a6715849c29050d42b3e41e492
Source dataset
uspto-grants-1977_05
Patent number
US04025634

Linked notes

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