Allyl bromide → (+/-)-trans-1-Allyl-4-(4-bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine

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Reaction Steps

The purified benzhydrylpiperazine (41.0 g, 83.7 mmol) was dissolved in 500 mL of dry tetrahydrofuran with 7.3 mL (84 mmol) of allyl bromide and 22 g (200 mmol) of sodium carbonate and heated at reflux overnight under nitrogen. The cooled reaction solution was filtered and the solvent removed to give 44.1 g of crude (±)-trans-1-allyl-4-(4-bromo-α-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine as a brown oil. NMR (200 MHz, CDCl3): δ 0.15 (s,6H) 0.95 (m,12H); 1.15 (2 overlapping d,J=6 Hz,3H); 1.8 (m,1H); 2.1 (m,1H); 2.35-2.65 (m,3H); 2.7-2.9 (m,2H); 3.35 (dd,J1 =5 Hz,J2 =12 Hz,1H); 5.0-5.2 (m,3H); 5.85 (m,1H); 6.6-7.5 (m,8H).

Provenance & Evidence