1,2,3,4-Tetrahydro-1-naphthylamine → HCID 69062509, compound

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Reaction Steps

9.6 g 1,1-carbonyldiimidazole (=CDl) dissolved in 85 ml THF was slowly added to a solution of 11.7 g of the 2,2-dimethyl-2H-chromen-6-yl acetic acid obtained above in 100 ml THF and stirred for 30 min. at room temperature. 8.8 ml 1,2,3,4-tetrahydro-1-naphthylamine, dissolved in 30 ml THF, was dropped slowly into this receiving solution, the resulting mixture was stirred for 1 hour and left to stand overnight at room temperature. The solvent was largely evaporated at reduced pressure, and the remaining residue was stirred with a mixture of diethyl ether and isopropanol (100:1 v/v) and crystallized. The resulting crystals were removed by suction and dried at 65° C. and 20 bar. Chromatography of the diethyl ether/isopropanol washing liquid on silica gel yielded further intermediate product, which was combined with the main quantity and dried. 17.5 g 2-(2,2-dimethyl-2H-chromen-6-yl)-N-1,2,3,4-tetrahydronaphth-1-yl acetamide was obtained as colorless solid, which was used without further purification for the subsequent reaction.

Provenance & Evidence