Water → (4-Methylpiperazin-1-yl)(4-nitrophenyl)methanone

Temperature

10 °C

A stirred solution of 1-methylpiperazine (14.6 mL) and triethylamine (19.2 mL) in dry dichloromethane (132 mL) at 10° C. was treated with 4-nitrobenzoyl chloride (23.2 g) portion wise whilst maintaining the temperature below 15° C. After stirring at 10° C. for a further 1 hour the reaction mixture was allowed to warn to room temperature and treated with water (100 mL). The organic phase was then separated and the aqueous phase further extracted with dichloromethane (50 mL). The combined organic extracts were washed with a 0.5 M aqueous solution of sodium carbonate (100 mL), then with brine (100 mL), and then evaporated to low bulk and treated with petroleum ether (80–100° C.) (100 mL). After removal of further solvent, and trituration, the insoluble material collected was washed with petroleum ether (40–60° C.) to give the title compound (30.4 g) as pale orange crystalline solid, m.p. 100–101° C. 1H NMR [(CDCl3]: δ 8.29 (d, 2H), 7.59 (d, 2H), 3.94–3.71 (bs, 2H), 3.52–3.29 (bs, 2H) and 2.58–2.30 (2×brs and s overlapping, 7H).

1. temperaturewhilst maintaining the temperature below 15° C
2. customto warn to room temperature
3. customThe organic phase was then separated
4. extractionthe aqueous phase further extracted with dichloromethane (50 mL)
5. washThe combined organic extracts were washed with a 0.5 M aqueous solution of sodium carbonate (100 mL)
6. customwith brine (100 mL), and then evaporated to low bulk
7. additiontreated with petroleum ether (80–100° C.) (100 mL)
8. customAfter removal of further solvent, and trituration
9. customthe insoluble material collected
10. washwas washed with petroleum ether (40–60° C.)

ORD record

ord-7014205f509347d484b4aa65cad694fb

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148215B2