Triethylamine → HCID 14990698, compound

To a solution of 4-chloro-3-nitrobenzyl alcohol (1 g) in methylene chloride (10 mL) were added triethylamine (1.12 mL) and methanesulfonyl chloride (0.5 mL) under ice-cooling, and the mixture was stirred at room temperature for 10 hours. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give (4-chloro-3-nitrobenzyl) mesylate (1.08 g). This material was dissolved in acetonitrile (4 mL)-ethanol (4 mL). To the solution were added 1,2,3,4-tetrahydroquinoline (1.62 g) and a catalytic amount of sodium iodide, and the mixture was stirred at 60° C. overnight. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1) to give 1-(4-chloro-3-nitrobenzyl)-1,2,3,4-tetrahydroquinoline (1.22 g). This material was dissolved in tetrahydrofuran (12 mL). To the solution were added methanol (12 mL), nickel (II) bromide (44 mg) and sodium borohydride (0.46 g) under ice-cooling, and the mixture was stirred at the same temperature for 30 minutes. Then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with ethyl acetate, and the resulting mixture was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1) to give the title compound (0.79 g).

1. temperaturecooling
2. washthe resulting mixture was washed with water and brine successively
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was removed under reduced pressure

ORD record

ord-6295d45b716940d59d94fa9287c92d31

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040693B2