Cysteamine Hydrochloride → 5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine

HRID 979787Notes

Reaction equation

HRID 979787 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[CH3:6][N:7]([CH2:9][C:10]1[O:14][C:13]([CH2:15]O)=[CH:12][CH:11]=1)[CH3:8].C([O-])([O-])=O.[Na+].[Na+]>Cl>[CH3:6][N:7]([CH2:9][C:10]1[O:14][C:13]([CH2:15][S:5][CH2:4][CH2:3][NH2:2])=[CH:12][CH:11]=1)[CH3:8]

Participants

5

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 10340Sodium CarbonateHCID 849065-((Dimethylamino)methyl)-2-furanmethanol

Product 1

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineYield 56%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Cysteamine hydrochloride (5.7 g; 0.05 mol) was dissolved in conc. hydrochloric acid (20 ml). Upon ice-cooling, 5-(dimethylamino)methyl-2-furanemethanol (7.75 g; 0.05 mol) was added. The reaction mixture was left to stand at 0° C. for 20 hours, added with a Na2CO3 excess, extracted with ether and filtered. The filtrate was evaporated to obtain an oily residue which after distillation in vacuo (p.e. 105°-107°; 0.1 mm) gave the pure product (6.0 g; 56% yield).

Workup

  1. temperatureUpon ice-cooling
  2. waitThe reaction mixture was left
  3. extractionextracted with ether
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customto obtain an oily residue which
  7. distillationafter distillation in vacuo (p.e. 105°-107°; 0.1 mm)
  8. customgave the pure product (6.0 g; 56% yield)

Sources & evidence

ORD record
ord-7d575e93e41c440cac13ebdb399ee948
Source dataset
uspto-grants-1987_01
Patent number
US04634701

Reaction notes

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