Sodium Hydroxide → 6-{4-[2-(4-Nitrophenyl)ethyl]piperazin-1-yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

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Reaction Conditions

Reaction Steps

A mixture of 6-piperazin-1-yl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (generated from treateding tert-Butyl 4-(6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl) piperazine-1-carboxylate (110 mg, 0.32 mmol) with trifluoroacetic acid (2 ml, 26 mmol) at RT), 1-(2-bromoethyl)-4-nitrobenzene (47 mg, 0.21 mmol), and Hunig's Base (0.054 ml, 0.31 mmol in 1 ml DMF was stirred at 60° C. for 21 hours. The reaction was shaken with 1 ml 1 N NaOH and 1 mL DCM. The organic layer was separated and evaporated to dryness. The residue was purified by mass directed HPLC to yield 6-{4-[2-(4-nitrophenyl)ethyl]piperazin-1yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile. LC-MS (IE, m/z): 391 [M+1]+. (0.050 μM)

Provenance & Evidence