Formaldehyde → 2-(beta-Dimethylaminoethyl)-5-methylpyrazine

HRID 2052289

Reaction equation

HRID 2052289 reaction equation
[CH3:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1.Cl.[CH3:10][NH:11][CH3:12].[CH2:13]=O.[OH-].[Na+]>O>[CH3:10][N:11]([CH3:13])[CH2:12][CH2:1][C:2]1[CH:7]=[N:6][C:5]([CH3:8])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 14798Sodium HydroxideHCID 312522,5-Dimethylpyrazine

Product 1

HCID 203776112-(beta-Dimethylaminoethyl)-5-methylpyrazineYield 34.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 75.0 g (0.7 mole) of 2,5-dimethylpyrazine and 41.0 g (0.5 mole) of dimethylamine hydrochloride was heated at 140° C. 60.0 g (38% aqueous solution) (0.75 mole) of formaldehyde was added over a period of two hours. After two hours additional heating the mixture was cooled. It was diluted with 110 ml of water, made basic with 10% sodium hydroxide and extracted with chloroform. The solvent was removed and the residue distilled to give 28.6 g of 2-(β-dimethylaminoethyl)-5-methylpyrazine, b.p. 106°-110° C. at 10 mm Hg.

Workup

  1. temperatureAfter two hours additional heating the mixture
  2. temperaturewas cooled
  3. extractionextracted with chloroform
  4. customThe solvent was removed
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-8e7c5d9d62e44642ad0dfac211e1259f
Source dataset
uspto-grants-1980_01
Patent number
US04183933

Linked notes

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