Ethanol, 2-[[(2,4-difluorophenyl)methyl]amino]- synthesis
- Product Name:Ethanol, 2-[[(2,4-difluorophenyl)methyl]amino]-
- CAS Number:1092287-13-2
- Molecular formula:C9H11F2NO
- Molecular Weight:187.19
Yield:1092287-13-2 69%
Reaction Conditions:
Stage #1: 2,4-difluorobenzaldehyde;ethanolaminewith sodium hydrogencarbonate in methanol at 20;Reflux;
Stage #2: with methanol;sodium tetrahydroborate at 0 - 20;
Steps:
6.6A
Ethanolamine (0.86 g, 14.07 mmol) was added to a solution of 2,4- difluorobenzaldehyde (2.0 g, 14.07 mmol) in methanol (50 mL) at RT. Sodium bicarbonate (7.0 g, 83.33 mmol) was added and the reaction mixture was stirred at reflux for 24 hours. The mixture was cooled to 0°C and sodium borohydride (0.32 g, 8.42 mmol) was then added in lots, maintaining the temperature of the mixture at 0- 5°C. The reaction mixture was was allowed to warm to RT over a period of 4 hours. The reaction mixture was then diluted with DCM (50 mL), washed with brine (2 x 30 mL), dried (Na2S04) and the solvents removed under reduced pressure to afford the title compound (1.79 g, 69%). The product was used in the next step without further purification.
References:
WO2011/141716,2011,A2 Location in patent:Page/Page column 89