2-Nitropropane → N-(2-Nitroisobutyl)piperidine

To a stirred ice cold solution of 2-nitropropane (10.0 g, 0.11 mol) and piperidine (11.1 mL, 1 equiv, 0.11 mol) was added dropwise a premixed solution of sodium hydroxide (0.5 mL, 5 N, 2 mol %) and a 37% aqueous solution of formaldehyde (8.4 mL g, 1 equiv, 0.11 mol) over 15 minutes maintaining an internal temperature between 10-15° C. The flask was removed from the ice bath and stirred at room temperature for 1 h. The reaction was then heated at 50° C. for 1 h. The biphasic mixture was cooled to room temperature and poured into a separatory funnel and diluted with ethyl acetate (150 mL) and water (50 mL). The layers were separated and the organic layer was washed with water (2×50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated to a yellow liquid (20.0 g). This material was used without further purification. 1H NMR (CDCl3, 400 MHz): δ 1.35-1.38 (m, 2H), 1.46-1.51 (m, 4H), 1.53 (s, 6H), 2.43-2.46 (t, J=5.2, 4H), 3.10 (s, 3H), 3.42-3.51 (m, 4H), 4.20 (s, 2H).

1. customThe flask was removed from the ice bath
2. temperatureThe reaction was then heated at 50° C. for 1 h
3. temperatureThe biphasic mixture was cooled to room temperature
4. additionpoured into a separatory funnel
5. additiondiluted with ethyl acetate (150 mL) and water (50 mL)
6. customThe layers were separated
7. washthe organic layer was washed with water (2×50 mL) and brine (50 mL)
8. dry with materialThe organic layer was dried over anhydrous MgSO4
9. filtrationfiltered
10. concentrationconcentrated to a yellow liquid (20.0 g)
11. customThis material was used without further purification

ORD record

ord-8bc484aec6d24a0ea9a589ec28782a24

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278482B2