5-((Dimethylamino)methyl)-2-furanmethanol → 2-[[5-(Dimethylamino)methyl-2-furanyl]methoxy]ethanamine

HRID 426475Notes

Reaction equation

HRID 426475 reaction equation
Cl.Cl[CH2:3][CH2:4][NH2:5].CC(C)([O-])C.[K+].[CH3:12][N:13]([CH2:15][C:16]1[O:20][C:19]([CH2:21][OH:22])=[CH:18][CH:17]=1)[CH3:14]>CN(C)C=O>[CH3:14][N:13]([CH2:15][C:16]1[O:20][C:19]([CH2:21][O:22][CH2:3][CH2:4][NH2:5])=[CH:18][CH:17]=1)[CH3:12]

Participants

5

Reactant 3

HCID 849065-((Dimethylamino)methyl)-2-furanmethanolHCID 97937372-Chloroethylamine hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 202133122-[[5-(Dimethylamino)methyl-2-furanyl]methoxy]ethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloroethylamine hydrochloride (6.25 g) in dry dimethylformamide was added dropwise to a stirred, cooled solution of potassium tert-butoxide (8.96 g) and 5-(dimethylamino)methyl-2-furanmethanol (12.4 g) in the same solvent. After 2 hr solvent was removed, the residue basified and extracted with ethyl acetate. The residue after removal of solvent was treated in ethanol with ethanolic oxalic acid. The crystalline salt was recrystallised from ethanol to give 2-[[5-(dimethylamino)methyl-2-furanyl]methoxy]ethanamine, bis oxalate, m.p. 130°-133° (3.05 g).

Workup

  1. customAfter 2 hr solvent was removed
  2. extractionthe residue basified and extracted with ethyl acetate
  3. customThe residue after removal of solvent
  4. additionwas treated in ethanol with ethanolic oxalic acid
  5. customThe crystalline salt was recrystallised from ethanol

Sources & evidence

ORD record
ord-4705c8f2ef594135a466feac7e34c538
Source dataset
uspto-grants-1979_10
Patent number
US04169855

Reaction notes

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