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

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.

1. customThe Grignard reaction
2. temperatureat reflux
3. additionby adding the bromebenzole
4. stirringThe mixture was stirred 2 h in a warm water bath
5. customquenched with 200 ml 6 M HCl solution at 0° C
6. filtrationThe reaction was filtered
7. washthe filtrate was washed with diethylether and water
8. dissolutionThe filtrate was dissolved in sodium carbonate solution
9. customThe layers were separated
10. washthe organic layer was washed with water
11. customevaporated

ORD record

ord-d3906f41f9b04f639f39a9069500af67

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741892B2