Sodium Iodide → 5-[(2-Oxopiperazin-1-yl)methyl]-5,6,7,8-tetrahydronaphthalene-1-carbonitrile

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Reaction Steps

A solution of tert-Butyl (2-{(chloroacetyl)[(5-cyano-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]amino}ethyl)carbamate (120 mg, 0.29 mmol) in DCM (5 mL) was added TFA (0.5 mL) and stirred at ambient temperature for 2 h until TLC indicated the starting material was consumed completely. The solvent was evaporated in vacuum. The residue was dissolved in ethanol (10 mL) and K2CO3 (120 mg, 0.9 mmol) and catalytic NaI was added. The reaction mixture was refluxed overnight, then the salt was removed by filtration. The filtrate was evaporated under vacuum, and then water (10 mL) and DCM (10 mL) was added. The mixture was extracted with DCM (10 mL×3), dried over anhydrous Na2SO4, and evaporated to give the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 7.42 (d, J=7.6 Hz, 1H), 7.33 (d, J=7.6 Hz, 1H), 7.15 (t, J=7.6 Hz, 1H), 3.66-3.72 (m, 1H), 3.54 (s, 2H), 3.21-3.32 (m, 4H), 2.98-3.11 (m, 3H), 2.75-2.85 (m, 1H), 1.78-1.94 (m, 2H), 1.71-1.75 (m, 2H).

Provenance & Evidence