Iodine → 1-(2,3-Dihydro-1-benzofuran-7-yl)methanamine

Temperature

0 °C

At 0° C., a solution of 2,3-dihydrobenzofuran-7-carboxylic acid amide (5.2 g, 31 mmol) in THF (100 ml) was added drop wise to a suspension of sodium borohydride in THF. The mixture was stirred for 20 min at 0° C. A solution of iodine (4.1 g, 16 mmol) in THF (100 ml) was added drop wise. After the addition was finished, the reaction mixture was heated for 16 hours to reflux. It was cooled to room temperature. Methanol (260 ml) was added drop wise. The solvent was removed in vacuo. The residue was dissolved in a 20% aqueous solution of sodium hydroxide (200 ml) and tert-butyl methyl ether (200 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (2×100 ml). The combined organic layers were dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using DCM/methanol/25% aqueous ammonia (100:10:1) as eluent to give 0.93 g of ((2,3-dihydrobenzofuran-7-yl)methyl)amine

1. additionAfter the addition
2. temperaturethe reaction mixture was heated for 16 hours
3. temperatureto reflux
4. temperatureIt was cooled to room temperature
5. customThe solvent was removed in vacuo
6. dissolutionThe residue was dissolved in a 20% aqueous solution of sodium hydroxide (200 ml) and tert-butyl methyl ether (200 ml)
7. customThe phases were separated
8. extractionThe aqueous phase was extracted with tert-butyl methyl ether (2×100 ml)
9. dry with materialThe combined organic layers were dried over magnesium sulphate
10. customThe solvent was removed in vacuo
11. customThe crude product was purified by flash chromatography on silica (90 g)

ORD record

ord-5666415465354a5091bf0f895283ba18

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1