Azepane → 1-[(5-Bromo-2-thienyl)methyl]hexahydro-1H-azepine

Temperature

0 °C

5-Bromo-2-thiophenecarbaldehyde (191 mg, 1 mmol) was diluted in a mixture of dichloromethane (6 mL) and N,N-dimethylformamide (2 mL), and cooled to 0° C. Hexahydro-1H-azepine (0.17 mL, 1.5 mmol, 1.5 eq) was added, followed by sodium triacetoxyborohydride (1.04 g, 4.9 mmol, 4.9 eq) and glacial acetic acid (2 drops). The mixture was stirred at 23° C. for 3 h. The reaction mixture was carefully quenched with saturated aqueous sodium bicarbonate. The reaction mixture was extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by isco combiflash, 40 g column, using a 0-70% ethyl acetate in hexanes gradient. The product fractions were concentrated to give the title compound as clear colorless oil (200 mg, 73%).

1. customThe reaction mixture was carefully quenched with saturated aqueous sodium bicarbonate
2. extractionThe reaction mixture was extracted with ethyl acetate
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by isco combiflash, 40 g column
7. concentrationThe product fractions were concentrated

ORD record

ord-51b19b0d62b8406c834d9497851dc70f

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372875B2