Formaldehyde → HCID 21419026, compound

HRID 441502Notes

Reaction equation

HRID 441502 reaction equation
CO.[CH3:3][O:4][C:5]1[C:6]([C:13]([O:15]C)=O)=[N:7][C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=1.[NH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH2:24][CH3:25].C=O>C(Cl)(Cl)Cl.ClCCl.O>[CH2:24]([N:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[CH2:18][NH:17][C:13]([C:6]1[C:5]([O:4][CH3:3])=[N:10][C:9]([CH3:11])=[C:8]([CH3:12])[N:7]=1)=[O:15])[CH3:25]

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 21419079HCID 21419079, compound

Product 1

HCID 21419026HCID 21419026, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To 20 ml. of methanol there was added 1.0 g of methyl 3-methoxy-5,6-dimethylpyrazine-2-carboxylate and 1.5 g of 2-aminomethyl-1-ethylpyrrolidine and the mixture was refluxed for 30 hours. The methanol was distilled off under reduced pressure from the reaction mixture, the residue thus obtained was added to a mixture of 20 ml. of water and 20 ml of dichloromethane and mixed well. The organic layer that was separated was acidified with an aqueous hydrochloric acid and extracted three times each time with 20 ml. of water. The aqueous extracts were combined basified with a 2 N aqueous sodium hydroxide and extracted three times each time with 20 ml. of dichloromethane. The dichloromethane extracts were combined, dried over anhydrous magnesium sulfate and then the solvent was distilled off. The residue thus obtained was applied to a silica gel column chromatography and then developed using a mixture of chloroform and methanal in a 1:1 volume ratio as the eluting solution, whereby 0.8 g. of light yellow oily N-(1 -ethylpyrrolidin-2-ylmethyl)-3-methoxy-5,6-dimethylpyrazine-2-carboxamide was obtained.

Workup

  1. temperaturethe mixture was refluxed for 30 hours
  2. distillationThe methanol was distilled off under reduced pressure from the reaction mixture
  3. customthe residue thus obtained
  4. additionwas added to a mixture of 20 ml
  5. customThe organic layer that was separated
  6. extractionextracted three times each time with 20 ml
  7. extractionextracted three times each time with 20 ml
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue thus obtained

Sources & evidence

ORD record
ord-6136da35ba38467b8b560cb034b519e3
Source dataset
uspto-grants-1977_08
Patent number
US04041032

Reaction notes

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