Iodine → (1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanol

Participants

Reaction Steps

136.6 g brombenzol in 300 mL diethylether was added to 21.2 g magnesium in 100 mL diethylether. The Grignard reaction is initiated with a small amount of iodine, kept at reflux by adding the bromebenzole and stirred additional 15 min for compleation. Then, 21.2 g 1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde in 300 mL diethylether was added. The mixture was stirred 2 h in a warm water bath and quenched with 200 ml 6 M HCl solution at 0° C. The reaction was filtered and the filtrate was washed with diethylether and water. The filtrate was dissolved in sodium carbonate solution and chloroform. The layers were separated and the organic layer was washed with water and evaporated to give 89.9 g of the desired product. Fp: 124° C.

Provenance & Evidence