Iodine → N-(2-(2-benzyloxyphenyl)ethyl)-N-methylamine

Temperature

0 °C

At 0° C., a solution of 2-(2-benzyloxyphenyl)-N-methylacetamide (9.39 g, 36.8 mmol) in tetrahydroufran (150 ml) was added dropwise to a suspension of sodium borohydride (1.67 g, 44.12 mmol) in tetrahydrofuran (100 ml). After the addition was finished, a solution of iodine (4.67 g, 18.39 mmol) in tetrahydrofuran (200 ml) was added dropwise. The solution was warmed to reflux for 16 h. It was cooled to 0° C. Methanol (200 ml) was added dropwise. The solvent was removed in vacuo. The residue was dissolved in an aqueous 20% sodium hydroxide solution (200 ml) and tert-butyl methyl ether (200 ml). The phases were separated. The aqueous phase was extracted with tert-butyl methyl ether (3×75 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 (400 g), using dichloromethane/methanol/25% aqueous ammonia as eluent (100:10:1), to give 4.38 g of N-(2-(2-benzyloxyphenyl)ethyl)-N-methylamine.

1. additionAfter the addition
2. temperatureThe solution was warmed
3. temperatureto reflux for 16 h
4. customThe solvent was removed in vacuo
5. dissolutionThe residue was dissolved in an aqueous 20% sodium hydroxide solution (200 ml) and tert-butyl methyl ether (200 ml)
6. customThe phases were separated
7. extractionThe aqueous phase was extracted with tert-butyl methyl ether (3×75 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 (400 g)

ORD record

ord-406add055946494cbb2324726b3cdbf5

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06127354