Benzyl Bromide → 1-Benzyl-4-(2-phenylethyl)-1,2,3,6-tetrahydropyridine

Temperature

100 °C

To a stirred solution of 120b (500 mg, 2.73 mmol) in DMF (5 ml) was added benzyl bromide (810 mg, 4.05 mmol) at 20-35° C. and the reaction mixture was stirred at 100° C. for 3 h. After 3 h, the reaction mixture was cooled to 20-35° C., diluted with ethanol (10 ml) and NaBH4 (110 mg, 2.97 mmol) was added slowly portion wise at 0° C., then heated at 100° C. for 1 h. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with NaOH solution at 20-35° C., excess ethanol was removed under vacuum and resultant residue was diluted with ethyl acetate (50 ml). The organic layer was washed with water (50 ml), brine (50 ml), dried over anhydrous Na2SO4 and evaporated. The crude compound was triturated with pet ether to get the desired compound as a yellow sticky solid (440 mg, 58%). 1H NMR (400 MHz, DMSO-d6) δ 7.56-7.43 (m, 5H), 7.38-7.7.28 (m, 2H), 7.27-7.20 (m, 2H), 7.19-7.12 (m, 1H), 5.44 (s, 1H), 4.61 (d, J=12.7 Hz, 1H), 4.41 (d, J=12.7 Hz, 1H), 3.62-3.56 (m, 2H), 3.39 (t, J=6.1 Hz, 2H), 2.79 (t, J=7.6 Hz, 2H), 2.62-2.52 (m, 2H), 2.41 (t, J=7.6 Hz, 2H).

1. waitAfter 3 h
2. temperaturethe reaction mixture was cooled to 20-35° C.
3. additionwas added slowly portion wise at 0° C.
4. temperatureheated at 100° C. for 1 h
5. customThe reaction mixture was quenched with NaOH solution at 20-35° C.
6. customexcess ethanol was removed under vacuum and resultant residue
7. additionwas diluted with ethyl acetate (50 ml)
8. washThe organic layer was washed with water (50 ml), brine (50 ml)
9. dry with materialdried over anhydrous Na2SO4
10. customevaporated
11. customThe crude compound was triturated with pet ether

ORD record

ord-a80e36b8fc6c4feab17d78884d0a9a97

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062002B2