2-(Dimethylamino)ethanol → HCID 21255081, compound

HRID 378228Notes

Reaction equation

HRID 378228 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].CC(C)([O-])C.[K+].Cl[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1>C1COCC1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 73277ChloropyrazineHCID 23665647Potassium tert-butoxide

Product 1

HCID 21255081HCID 21255081, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-dimethylaminoethanol (1 mL) in THF (20 mL) was treated with potassium tert-butoxide (1.2 g). After 5 min, chloropyrazine (2 g) was added and the reaction stirred 2 h. The solvent was evaporated, the residue suspended in cold water, the mixture acidified, and the mixture extracted with ether. The aqueous fraction was made basic and extracted with EtOAc. The extracts were dried, the solvent evaporated, and the residue purified by radial chromatography eluting with 10%-EtOH-1%--NH4OH--CHCl3 to give 2-(2-dimethylaminoethoxy)pyrazine (1.3 g). The HCl salt crystallized from 2-propanol as a white solid, m.p. 151-153° C. (Compound 26).

Workup

  1. customThe solvent was evaporated
  2. extractionthe mixture extracted with ether
  3. extractionextracted with EtOAc
  4. customThe extracts were dried
  5. customthe solvent evaporated
  6. customthe residue purified by radial chromatography
  7. washeluting with 10%-EtOH-1%

Sources & evidence

ORD record
ord-591c9d2b77564c9e9f67b9da8633ba0c
Source dataset
uspto-grants-2000_02
Patent number
US06030966

Reaction notes

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