Hydrochloric Acid → trans-N-(6,7-dichloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Participants

Reaction Steps

N-chlorosuccinimide (6.87 mg, 0.05 mmol) and 0.5 μL 1N HCl was added to trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (20 mg, 0.05 mmol) in 102 μL of acetone. The resulting mixture was stirred at room temperature for 18 h. No reaction was observed. The reaction was repeated under the same conditions. The resulting mixture was stirred at room temperature for 1.5 h. The organic layer was washed with saturated aq. sodium bicarbonate and water, dried (Na2SO4) and evaporated and the crude compound was purified by preparative HPLC to give trans-N-(6,7-dichloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (3.6 mg, 17%) and trans-N-(7,8-dichloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (1.6 mg, 7%). Data: (m/z)=431 (M+H)+.

Provenance & Evidence