Reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[O:15]1[CH2:19][CH2:18][CH2:17][CH:16]1[C:20](Cl)=[O:21].C(OCC)(=O)C>C1C=CC=CC=1.CCOCC.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6](=[CH:5][CH:4]=1)[NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][C:20]([CH:16]1[CH2:17][CH2:18][CH2:19][O:15]1)=[O:21]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
5-Methoxytryptamine (540 mg, 2.84 mmole) was suspended in benzene (5 ml). The mixture was cooled in an ice bath and a solution of tetrahydro-2-furoyl chloride (390 μl, 3.7 mmole) in benzene (5 ml) was slowly added. The reaction, mixture was stirred at room temperature for 15 hours and was diluted with ether (25 ml). It was extracted with water (25 ml), NaHCO3 solution (2×25 ml) and saturated NaCl solution (25 ml) dried (MgSO4) and the solvent was removed in vacuo. Further purification was obtained by column chromatography on silica gel. The solvent was 50% ethyl acetate in CH2Cl2. Fractions of 10 ml were collected and the product was eluted in fractions 19-32. The product was obtained as an oil. The yield was 220 mg (−30%).
Workup
- temperatureThe mixture was cooled in an ice bath
- customThe reaction, mixture
- extractionIt was extracted with water (25 ml), NaHCO3 solution (2×25 ml) and saturated NaCl solution (25 ml)
- dry with materialdried (MgSO4)
- customthe solvent was removed in vacuo
- customFurther purification
- customwas obtained by column chromatography on silica gel
- customFractions of 10 ml were collected
- washthe product was eluted in fractions 19-32
- customThe product was obtained as an oil
Sources & evidence
- ORD record
- ord-200b457f636045d7be5483b0b0638938
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06858642B1
Linked notes
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