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ChemicalBook CAS DataBase List (3R,6R)-3,6-Bis[(aminooxy)methyl]-2,5-piperazinedione
16337-02-3

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

2synthesis methods
-

Yield: 85%

Reaction Conditions:

with acetic acid in ethanol for 6 h;Reflux;

Steps:

(3R,6R)-3,6-Bis[(aminooxy)methyl]piperazine-2,5-dione (1a)
Acetic acid (20 ml) was added dropwise at room temperature to a solution of compound 1 (10 g, 0.10 mol)in ethanol (200 ml). The reaction mixture was refluxed for 6 h. The reaction mixture was cooled to 0-5°C on an ice bath and stirring continued for 1 h. Pure product was isolated by filtration, washed with cold ethanol (5×2 ml),and dried under reduced pressure at 45°C to afford product 1a. Yield 8.5 g (85%), white solid, mp 175-180°C (decomp.) (mp 180°C (decomp., EtOH)29). IR spectrum,ν, cm-1: 1666 (C=O), 3184-3338 (HN). 1H NMR spectrum (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.

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]

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