ChemicalBook CAS DataBase List 3,6-Methylene-2,5-piperazinedione

3,6-Methylene-2,5-piperazinedione synthesis

3synthesis methods

Product Name:3,6-Methylene-2,5-piperazinedione
CAS Number:15996-22-2
Molecular formula:C6H6N2O2
Molecular Weight:138.12

16337-02-3 Synthesis

(3R,6R)-3,6-Bis[(aminooxy)methyl]-2,5-piperazinedione

16337-02-3
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15996-22-2
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Yield:15996-22-2 80%

Reaction Conditions:

with sodium hydroxide in water at -5 - 30; for 20 h;

Steps:

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 dropwiseat -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 driedunder reduced pressure at 50°C to afford product 1b. Yield 5.5 g (80%), white solid, mp 380-390°C (decomp.)(mp >300°C ³⁰). 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 NMRspectrum (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.

References:

Awasthi, Arun Kumar;Kumar, Brijesh;Aga, Mushtaq A;Tripathi, Punit;Reddy, Cirandur Suresh;Kumar, Pramod [Chemistry of Heterocyclic Compounds,2017,vol. 53,# 11,p. 1248 - 1253][Khim. Geterotsikl. Soedin.,2017,vol. 53,# 11,p. 1248 - 1253,6]

2,5-Piperazinedione, 3,6-bis[(acetyloxy)methyl]-

5249-15-0
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15996-22-2
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References

5625-41-2 Synthesis

3,6-BIS(HYDROXYMETHYL)-2,5-PIPERAZINEDIONE

5625-41-2
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15996-22-2
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References