2-(Dimethylamino)ethanol → HCID 21255081, compound

HRID 636355Notes

Reaction equation

HRID 636355 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%—NH4OH—CHCl3

Sources & evidence

ORD record
ord-1efd64aefe794d0cbe842098489eb3a6
Source dataset
uspto-grants-2001_02
Patent number
US06194416B1

Reaction notes

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