4-[(4-bromophenyl)methyl]piperazin-2-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-bromobenzyl bromide (1.0 g, 4.0 mmol), triethylamine (0.84 mL, 6.0 mmol) and piperazin-2-one (0.81 g, 8.0 mmol) in THF (20 mL) was stirred at ambient temperature for 16 h. The solvent was evaporated and the resultant residue diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound (1.0 g, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.49-7.43 (m, 2 H); 7.24-7.16 (m, 2 H); 6.20 (s, 1 H); 3.53 (s, 2 H); 3.38-3.32 (m, 2 H); 3.15 (s, 2 H); 2.66-2.59 (m, 2 H).). LCMS (Method G): RT=2.54 min, M−H+=268. The solvent was evaporated the resultant residue diluted with saturated aqueous sodium bicarbonate solution extracted with ethyl acetate (2×50 mL) The combined organic layer was dried over sodium sulfate filtered evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-bromobenzyl bromide (1.0 g, 4.0 mmol), triethylamine (0.84 mL, 6.0 mmol) and piperazin-2-one (0.81 g, 8.0 mmol) in THF (20 mL) was stirred at ambient temperature for 16 h. The solvent was evaporated and the resultant residue diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered and evaporated to afford the title compound (1.0 g, 93%). 1H NMR (CDCl3, 300 MHz): δ 7.49-7.43 (m, 2H); 7.24-7.16 (m, 2H); 6.20 (s, 1H); 3.53 (s, 2H); 3.38-3.32 (m, 2H); 3.15 (s, 2H); 2.66-2.59 (m, 2H).). LCMS (Method G): RT=2.54 min, M−H+=268. The solvent was evaporated the resultant residue diluted with saturated aqueous sodium bicarbonate solution extracted with ethyl acetate (2×50 mL) The combined organic layer was dried over sodium sulfate filtered evaporated