Iodine → N-Methyl-N-(2-phenoxybenzyl)amine

Temperature

0 °C

At 0° C., a solution of N-methyl-2-phenoxybenzamide (22.2 g, 97.7 mmol) in THF (175 ml) was added dropwise to a suspension of sodium borohydride (9.20 g, 244 mmol) in THF (100 ml). The reaction mixture was stirred at 0° C. for 20 min. A solution of iodine (24.8 g 97 mmol) in THF (125 ml) was added dropwise. The reaction mixture was heated to 70° C. for 16 hours. It was cooled to 0° C. Methanol 500 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 (3×100 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 (300 g), using a mixture of DCM/methanol/25% aqueous ammonia as eluent, to give 3.04 g of N-methyl-N-(2-phenoxybenzyl)amine.

1. temperatureThe reaction mixture was heated to 70° C. for 16 hours
2. temperatureIt was cooled to 0° C
3. customThe solvents were removed in vacuo
4. dissolutionThe residue was dissolved in a mixture of tert-butyl methyl ether (200 ml)
5. customThe phases were separated
6. extractionThe aqueous phase was extracted with tert-butyl methyl ether (3×100 ml)
7. dry with materialThe combined organic layers were dried over magnesium sulphate
8. customThe solvent was removed in vacuo
9. customThe crude product was purified by flash chromatography on silica (300 g)
10. additiona mixture of DCM/methanol/25% aqueous ammonia as eluent

ORD record

ord-25f404b2732846958cb2446c881a44e0

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06437147B1