Dichloromethane → N-(cyclopentylmethyl)-N-ethylamine

To a suspension of (3-{[(3,5-bis-trifluoromethyl-benzyl)-(1H-tetrazol-5-yl)-amino]-methyl}-quinolin-2-yl)-cyclopentylmethyl-ethyl-amine (0.133 g, 0.230 mmol in water (4 mL) was added sodium hydroxide (0.009 g, 0.230 mmol), and this mixture was stirred for 15 min at RT, followed by the addition of dichloromethane (4 mL). To this reaction mixture was added dimethyl sulfate (0.030 g, 0.241 mmol), followed by the addition of tetrabutylammonium bromide (0.003 g, 0.011 mmol). This mixture was stirred for 24 h. The organic layer was separated from aqueous layer, the aqueous layer was extracted with DCM (3×10 mL), the combined organic layer was washed with brine and dried over sodium sulfate, and concentrated under vacuum to afford the crude residue. This residue was purified by column chromatography over 100-200 mesh silica gel using 8% ethyl acetate and petroleum ether to afford (3-{[3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazole-5-yl)-amino]-methyl-}-quinoline-2-yl)-cyclopentylmethyl-ethyl amine (0.030 g, yield: 22%).

1. stirringThis mixture was stirred for 24 h
2. customThe organic layer was separated from aqueous layer
3. extractionthe aqueous layer was extracted with DCM (3×10 mL)
4. washthe combined organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated under vacuum
7. customto afford the crude residue
8. customThis residue was purified by column chromatography over 100-200 mesh silica gel using 8% ethyl acetate and petroleum ether

ORD record

ord-4dd6eff52ef94a5ca16994b30e25359e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604055B2