Sodium Iodide → 4-((alpha-R)-alpha-((2S,5R)-2,5-Dimethyl-4-(2-fluorobenzyl)-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide

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Reaction Steps

By a procedure essentially identical to that of Example 3, the title compound was prepared from 1.23 g (3.00 mmol) of 4-((alpha-R)-alpha-((2S,5R)-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide, 2-fluorobenzyl bromide (724 μL, 6.0 mmol), sodium iodide (45 mg, 0.30 mmol), and triethylamine (1.51 mL, 10.8 mmol). The crude product was slurried with 1:1 saturated sodium carbonate/water for several hours with manual crushing of suspended solids. Crystalline product was collected by filtration, washed with water and dried to give 1.494 g of 4-((alpha-R)-alpha-((2S,5R)-2,5-dimethyl-4-(2-fluorobenzyl)-1-piperazinyl)-3-methoxybenzyl)-N,N-diethylbenzamide as a white solid. Calc. for C32H40FN3O2 0.1 H2O: C, 73.99; H, 7.80; N, 8.09; F, 3.66. Found C, 73.98; H, 7.86; N, 8.00; F, 3.77. 1H NMR (CDCl3, 300 MHz); δ 1.09 (d, J˜7 Hz, 3H); 1.11 (d, J˜7 Hz, 3H); 1.945 (apparent t, J˜9 Hz, 1H); 2.07 (apparent t, J˜9 Hz, 1H); 2.59 (m, 2H); 2.63 (d, J˜11 Hz, 1H); 2.73 (d, J˜11 Hz, 1H); 3.28 (brd m, 2H); 3.33 (half of ABq, J˜14 Hz, 1H); 3.54 (brd m, 2H); 3.78 (s, 3H); 3.88 (half of ABq, J˜14 Hz, 1H); 5.14 (s, 1H); 6.74 (s, 1H); 6.80 (m, 2H); 7.00 (t, J˜8 Hz, 1H); 7.07 (t, J˜7 Hz, 1H); 7.22 (m, 2H); 7.29 (half of ABq, J˜8 Hz, 2H); 7.37 (t, J˜7 Hz, 1H); 7.47 (half of ABq, J˜8 Hz, 2H).

Provenance & Evidence