Chemistry of Heterocyclic Compounds 2017, 53(11), 1248–1253
7. (a) Hall, R. G.; Leff, R. D.; Gumbo, T. Pharmacotherapy
(D2O), δ, ppm (J, Hz): 3.84 (2H, dd, J = 10.8, J = 3.2,
CH2); 3.98 (2H, dd, J = 10.8, J = 4.8, CH2); 4.24 (2H, t,
J = 3.6, 2CHCH2). 13C NMR spectrum (D2O), δ, ppm: 54.3
(2C); 75.6 (2C); 167.8 (2C). Mass spectrum, m/z (Irel,%):
205 [M+H]+ (100). Found, %: C 35.30; H 5.91; N 27.45.
C6H12N4O4. Calculated, %: C 35.29; H 5.92; N 27.44.
3,6-Dimethylidenepiperazine-2,5-dione (1b). A stirring
solution of compound 1a (10 g, 0.05 mol) in water (250 ml)
was cooled to –5–0°C on an ice bath. A solution of NaOH
(160 mg, 0.004 mol) in water (50 ml) was added dropwise
at –5 –0°C. The reaction mixture was warmed up to 25–30°C,
and product starts to precipitate. The reaction mixture was
stirred at 25–30°C for 20 h. Pure product was isolated by
filtration, washed with cold ethanol (5×3 ml), and dried
under reduced pressure at 50°C to afford product 1b. Yield
5.5 g (80%), white solid, mp 380–390°C (decomp.)
(mp >300°C30). IR spectrum, ν, cm–1: 1687 (C=O), 3182
(NH). 1H NMR spectrum (DMSO-d6), δ, ppm: 4.91 (2H, s,
CH2); 5.26 (2H, s, CH2); 10.89 (2H, s, 2NH). 13C NMR
spectrum (DMSO-d6), δ, ppm: 100.9 (2C); 135.1 (2C);
156.6 (2C). Mass spectrum, m/z (Irel,%): 137 [M–H]– (100).
Found, %: C 52.15; H 4.41; N 20.29. C6H6N2O2.
Calculated, %: C 52.17; H 4.38; N 20.28.
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1
A Supplementary information file containing H and
13C NMR spectra and HPLC analysis of the synthesized
compounds is available at the journal website at http://
link.springer.com/journal/10593.
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