Cysteamine Hydrochloride → 2-{(5-{[N-methyl-N-propargylamino]methyl}-2-furyl)methylthio}ethylamine
Reaction equation
[CH3:1][N:2]([CH2:6][C:7]1[O:11][C:10]([CH2:12]O)=[CH:9][CH:8]=1)[CH2:3][C:4]#[CH:5].Cl.[NH2:15][CH2:16][CH2:17][SH:18].[OH-].[Na+]>Cl.O>[CH3:1][N:2]([CH2:6][C:7]1[O:11][C:10]([CH2:12][S:18][CH2:17][CH2:16][NH2:15])=[CH:9][CH:8]=1)[CH2:3][C:4]#[CH:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 5-{[N-methyl-N-(2-propynyl)amino]methyl}-2-furanmethanol (40.0 g; 223 mmoles) [prepared in Step A] in 100 ml of ice-cold concentrated HCl was added to a cold (5°) stirred solution of cysteamine hydrochloride (27.9 g, 24.6 mmoles) in 125 ml of concentrated hydrochloric acid. The solution was allowed to stand at 0° for 21/2 days, and then at ambient temperature for 7 hours to complete the reaction. The reaction mixture was cooled in an ice-water bath, diluted with 200 ml of water, made strongly alkaline with 40% aqueous NaOH, and then extracted with three portions of methylene chloride. The combined organic phase was dried, filtered, and evaporated under reduced pressure to give the product as a thick oil (46.4 g). A rapid vacuum distillation of the oil yielded the title compound, bp 136°-140°/0.2 mm Hg.
Workup
- customto stand at 0° for 21
- custom2 days
- customthe reaction
- temperatureThe reaction mixture was cooled in an ice-water bath
- extractionextracted with three portions of methylene chloride
- customThe combined organic phase was dried
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-a6346f9579d54d87be6a8f3e721aefbd
- Source dataset
- uspto-grants-1985_04
- Patent number
- US04510309
Reaction notes
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