[N+:1]([CH:4]([CH3:6])[CH3:5])([O-:3])=[O:2].[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10][NH2:11].[OH-].[Na+].[CH2:15]=O>CC(O)C.O>[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10][NH:11][CH2:5][C:4]([CH3:15])([N+:1]([O-:3])=[O:2])[CH3:6]
To a solution of 2-nitropropane (2.07 g, 23.2 mmol) and N1,N1-dimethyl-ethane-1,2-diamine (2.22 g, 25.2 mmol) in 2-propanol (5 ml) was added 5 M NaOH in H2O (30 ul, 0.15 mmol), H2O (1 ml). 37% Formaldehyde in H2O (1.8 ml, 24 mmol) was added dropwise, and the reaction stirred for 22 h. The solution was concentrated in vacuo to half volume, acidified with sat. NaHSO4 to pH 2, and washed with 3× 100 ml CH2Cl2. 15% NaOH in H2O was added to pH 12, and the slurry extracted with 3× 100 ml CH2Cl2. The organic phases were combined, dried on MgSO4, concentrated in vacuo, and used without further purification. ESI/APCI (pos) expected for C8H19N3O2: 189.15. Found: 190 (MH+).
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