Iodine → 2-(2-(2-(Methylamino)ethyl)phenoxy)ethanol

At 0° C., a solution of ethyl 2-(2-((N-methylcarbamoyl)methyl)phenoxy)acetate (5.00 g, 19.9 mmol) in tetrahydrofuran (75 ml) was added dropwise to a suspension of sodium borohydride (2.26 g, 59.7 mmol) in tetrahydrofuran (75 ml). A solution of iodine (5.05 g, 19.9 mmol) in tetrahydrofuran (150 ml) was added dropwise. The solution was warmed to room temperature and heated to reflux for 16 h. It was cooled to 0° C. Methanol (150 ml) was added dropwise. The solvent was removed in vacuo. The solid residue was dissolved in 20% aqueous sodium hydroxide solution/tert-butyl methyl ether (150 ml/150 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (3×150 ml). The combined organic layers were dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (80 g), using dichloromethane/methanol/10% aqueous ammonia (first: 100:10:1, then 70:30:3) as eluent, to give 1.124 g of 2-(2-(2-(Methylamino)ethyl)phenoxy)ethanol.

1. temperatureheated
2. temperatureto reflux for 16 h
3. temperatureIt was cooled to 0° C
4. customThe solvent was removed in vacuo
5. dissolutionThe solid residue was dissolved in 20% aqueous sodium hydroxide solution/tert-butyl methyl ether (150 ml/150 ml)
6. customThe phases were separated
7. extractionThe aqueous phase was extracted with tert-butyl methyl ether (3×150 ml)
8. dry with materialThe combined organic layers were dried over magnesium sulfate
9. customThe solvent was removed in vacuo
10. customThe crude product was purified by flash chromatography on silica (80 g)

ORD record

ord-50d0b51b77294492ab9df510b34aad16

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127354