Reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][OH:11])=[CH:7][CH:6]=1)[CH3:3].[CH2:12]1[NH:14][CH2:13]1.CS(O)(=O)=O>O1CCCC1>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][O:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:1]Participants
Procedure
To a solution of 5-(dimethylamino)methyl-2-furanmethanol (6.2 g) and ethylene imine (2.82 g) in dry tetrahydrofuran was added a solution of methanesulphonic acid (11.6 g) in tetrahydrofuran (40 ml). The solution was evaporated and the oily residue heated at 98°-100° for 10 mins. After 18 hr, 5N sodium hydroxide (60 ml) was added and the solution evaporated to dryness. Anhydrous sodium sulphate and ethyl acetate (150 ml) were added and after 2 hr the suspension was filtered, treated with decolourising charcoal and evaporated. The resulting oil was chromatographed on silica, firstly with methanol-ammonia 0.88 79:1, and the eluate discarded, and secondly with methanol-ammonia 0.88 19:1. This eluate was evaporated to give an oil from which the bisoxalate salt of 2-[[5-(dimethylamino)methyl-2-furanyl]methoxy]ethanamine (from ethanol) 0.2 g, m.p. 125°-128°, was obtained. Route (ii)
Workup
- customThe solution was evaporated
- temperaturethe oily residue heated at 98°-100° for 10 mins
- addition5N sodium hydroxide (60 ml) was added
- customthe solution evaporated to dryness
- additionAnhydrous sodium sulphate and ethyl acetate (150 ml) were added and after 2 hr the suspension
- filtrationwas filtered
- additiontreated with decolourising charcoal
- customevaporated
- customThe resulting oil was chromatographed on silica, firstly with methanol-ammonia 0.88 79:1
- customThis eluate was evaporated
Sources & evidence
- ORD record
- ord-455eb8b5e01d44359c3ecf6e15714f60
- Source dataset
- uspto-grants-1978_12
- Patent number
- US04128658
Linked notes
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