Allyl bromide → (+/-)-3-(alpha-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide

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Reaction Steps

(±)-3-(α-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide was prepared from 3-(3-((tert-butyldimethyl-silyl)oxy)-α-chlorobenzyl)-N,N-diethylbenzamide (Example 1, infra) and cis-2,6-dimethylpiperazine according to the methods of Example 1. This material was then alkylated with allyl bromide and deprotected by methods similar to that in Example 4 to give (±)-cis-3-(α-(4-allyl-3,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide. NMR (DMSO-d6, 200 MHz): δ0.87 (d, J=3.9 Hz, 3H); 0.90 (d, J=3.9 Hz, 3H); 0.940-1.22 (m, 6H); 1.65 (t, J=10.7 Hz, 2H); 2.55-2.75 (m, 4H); 3.00-3.22 (m, 2H); 3.22-3.54 (m, 4H); 4.16 (s, 1H); 5.15 (dd, J1 =2.2 Hz, J2 =10.0 Hz, 1H); 5.22 (d, J=14.8 Hz, 1H); 5.96 (m, 1H); 6.58 (d, J=8.0 Hz, 1H); 6.82 (d, J=7.3 Hz, 1H); 6.84 (s, 1H); 7.02-7.20 (m, 2H); 7.30-7.46 (m, 3H); 9.33 (s, 1H). Mass spectrum (CI--CH4) m/e: 436 (M+1. 100%). The monohydrochloride salt was prepared as in Example 4. Calc. for C27H37N3O2HCl 0.75 H2O: C, 66.78: H, 8.20; N, 8.65; Cl, 7.30. Found: C, 66.84; H, 8.28; N, 8.53; Cl, 7.25.

Provenance & Evidence