Benzo(B)Thiophene → HCID 9861313, compound

To a solution of benzothiophene (3 g, 22.4 mmol) in anhydrous tetrahydrofuran (50 ml) at -10° C. under nitrogen was added n-butyllithium (9.83 ml of a 2.5M solution in toluene), the mixture was allowed to warm to room temperature and stirred for 1 hr. The reaction mixture was cooled to -40° C. and 1-benzyl-4-piperidone (4.23 g, 22.4 mmol) added, allowed to warm to room temperature and stirred for 14 hr. The reaction mixture was concentrated in vacuo and trifluoroacetic acid (10 ml) added. This mixture was stirred at room temperature for 14 hr and then concentrated in vacuo. The product was extracted into dichloromethane (3×100 ml) from aqueous potassium carbonate. The organic layer was washed with water (1×50 ml), brine (1×50 ml) and dried (MgSO4). After concentration of the extracts the crude product was purified using silica gel column chromatography to yield the title compound (4.2 g, 68%) as a colourless oil; δH (CDCl3) 2.64 (2H, m, tetrahydropyridinyl CH2), 2.74 (2H, m, tetrahydropyridinyl CH2), 3.18 (2H, m, tetrahydropyridinyl CH2), 3.65 (2H, s, PhCH2N), 6.18 (1H, m, CH=CR), 7.11 (1H, s, 3'-H), and 7.24-7.73 (9H, m, Ar--H).

1. temperatureThe reaction mixture was cooled to -40° C.
2. temperatureto warm to room temperature
3. stirringstirred for 14 hr
4. concentrationThe reaction mixture was concentrated in vacuo and trifluoroacetic acid (10 ml)
5. additionadded
6. stirringThis mixture was stirred at room temperature for 14 hr
7. concentrationconcentrated in vacuo
8. extractionThe product was extracted into dichloromethane (3×100 ml) from aqueous potassium carbonate
9. washThe organic layer was washed with water (1×50 ml), brine (1×50 ml)
10. dry with materialdried (MgSO4)
11. customAfter concentration of the extracts the crude product was purified

ORD record

ord-f8541bae4e3d42e188663a20f99f0c81

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05700809