Iodine → N-methyl-N-[2-(1-naphthyloxy)ethyl]amine

Temperature

70 °C

At 0° C., a solution of N-methyl-2-(1-naphthyloxy)acetamide (17.4 g, 81.1 mmol) in THF (100 ml) was added dropwise to a suspension of sodium borohydride (7.35 g, 195 mmol) in THF (100 ml). The reaction mixture was stirred for 15 min at this temperature. A solution of iodine (20.6 g, 81 mmol) in THF (200 ml) was added dropwise. The reaction mixture was heated to 70° C. for 16 hours. It was cooled to 0° C. Methanol (250 ml) was added dropwise. The solvents were removed in vacuo. The residue was dissolved in a mixture of tert-butyl methyl ether (200 ml) and a 20% aqueous solution of sodium hydroxide (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 crude product was purified by flash chromatography on silica (200 g), using DCM/methanol/25% aqueous ammonia (100:10:1) as eluent, to give 1.94 g of N-methyl-N-[2-(1-naphthyloxy)ethyl]amine.

1. temperatureIt was cooled to 0° C
2. customThe solvents were removed in vacuo
3. dissolutionThe residue was dissolved in a mixture of tert-butyl methyl ether (200 ml)
4. customThe phases were separated
5. extractionThe aqueous phase was extracted with tert-butyl methyl ether (2×100 ml)
6. dry with materialThe combined organic layers were dried over magnesium sulphate
7. customThe crude product was purified by flash chromatography on silica (200 g)

ORD record

ord-0f86354fb3694391a7724b900b21a10d

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1