Ethanol, reaction products with ammonia, distn. residues → 2-(7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)ethan-1-amine

温度

50 °C

To a solution of (1,2,3,4-tetrahydro-7-methoxy-1-naphthylidene)acetonitrile (1.0 g, 5.02 mmol) in ethanol (10 ml) were added a saturated ammonia/ethanol solution (5 ml) and Raney nickel (W-2, 1 g). The mixture was stirred for 4 hours at 50° C. under hydrogen atmosphere (3-4 kgf/cm2). The Raney nickel was filtered off and, then, the solvent was distilled off under reduced pressure to give 1-(2-aminoethyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene. To a solution of this 1-(2-aminoethyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene and triethylamine (0.76 g, 7.53 mmol) in THF (20 ml) was gradually added dropwise, under ice-cooling, cyclopropanecarbonyl chloride (0.63 g, 6.02 mmol). The mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into water. The organic layer was subjected to extraction with chloroform. The extract solution was washed with brine and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8) to give the above-titled compound (1.04 g, yield 76%, oil).

1. filtrationThe Raney nickel was filtered off
2. distillationthe solvent was distilled off under reduced pressure

ORDレコード

ord-0004cdf0a5224b64ac5d2f4fa99d6324

出典データセット

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06235789B1