Sodium Hydroxide → 4-(4-bromo-1-(3-chloro-2-methylbenzyl)-1H-benzo[d]imidazol-6-yl)morpholine

Participants

Reaction Conditions

Reaction Steps

Into a 100 ml round bottomed flask with 4-bromo-1-(3-chloro-2-methylbenzyl)-1H-benzo[d]imidazol-6-amine (2.33 g, 6.64 mmol), tetrabutylammonium iodide (0.123 g, 0.332 mmol) was added 6N sodium hydroxide (16.61 ml, 100 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (1.657 ml, 13.29 mmol). The reaction was heated to 110° C. for 2 h, cooled to room temperature and the mixture was extracted with EtOAc. The combined organic phase was washed with Brine (20 mL) and concentrated. The residue was purified by reversed phase HPLC and was eluted with a gradient of acetonitrile (0.1% TFA) and water (0.1% TFA v/v) (30-65%) over 12 minutes. The appropriate fractions were collected and evaporated to yield 4-(4-bromo-1-(3-chloro-2-methylbenzyl)-1H-benzo[d]imidazol-6-yl)morpholine (483 mg, 1.148 mmol, 17.28% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.37 (s, 3H) 3.14-3.22 (m, 4H) 3.84-3.93 (m, 4H) 5.48 (s, 2H) 6.71 (d, J=2.02 Hz, 1H) 6.91 (d, J=7.58 Hz, 1H) 7.16 (t, J=7.83 Hz, 1H) 7.34 (d, J=2.02 Hz, 1H) 7.44 (d, J=7.58 Hz, 1H) 8.84 (br. s., 1H); LC/MS: MS (ES+) m/e 421 [M+H]+.

Provenance & Evidence