Water → HCID 21832605, compound

Temperature

-15 °C

To a 1 L three-necked flask equipped with a magnetic stir bar, reflux condenser and addition funnel, was added bromo acetyl bromide (82.8 g, 0.41 mole) in CHCl3 (170 mL). The addition funnel was charged with a solution of piperazine (0.2 mole, 17.2 g) and triethylamine (70 mL) in CHCl3 (180 mL). The flask was chilled to -15° C. by means of a CH3CN/liquid N2 bath, and the amine was slowly added to the acid bromide. After the addition was complete the mixture was allowed to warm to ambient temperature and was stirred for 1 hour. The flask was then cooled to 0° C. and H2O (100 mL) was slowly added. The mixture was diluted with CHCl3 (500 mL) and the layers were separated. The organic layer was extracted with H2O (5×50 mL), 0.05N NaOH (5×50 mL) and H2O (200 mL), and dried (Na2SO4). The dark orange solution was filtered and concentrated to a beige solid. The material was purified by filtration through a bed of silica gel. The product eluted with 2-5% methanol/CH2Cl2. After combining and concentrating the desired fractions, 15.0 g (49.2%) of a white solid was obtained. The title product was recrystallized from warm 2-propanol (400 mL) affording 9.95 g. 1H NMR (CDCl3): δ 3.61 (dt, 6 H), 3.85 (s, 4 H).

1. customTo a 1 L three-necked flask equipped with a magnetic stir bar
2. temperaturereflux
3. additioncondenser and addition funnel
4. additionAfter the addition
5. temperatureto warm to ambient temperature
6. temperatureThe flask was then cooled to 0° C.
7. customthe layers were separated
8. extractionThe organic layer was extracted with H2O (5×50 mL), 0.05N NaOH (5×50 mL) and H2O (200 mL)
9. dry with materialdried (Na2SO4)
10. filtrationThe dark orange solution was filtered
11. concentrationconcentrated to a beige solid
12. filtrationThe material was purified by filtration through a bed of silica gel
13. washThe product eluted with 2-5% methanol/CH2Cl2
14. concentrationconcentrating the desired fractions

ORD record

ord-f3162d73085e4feeae7e243985cbedc9

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05650133