Methanol → HCID 59355185, compound
Reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][NH:5][CH2:6][C:7]([CH3:10])([NH2:9])[CH3:8].C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.CO>C(Cl)Cl>[CH3:11][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[CH2:6][C:7]([CH3:8])([CH3:10])[NH:9][C:17]1=[O:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N1-(2-(dimethylamino)ethyl)-2-methylpropane-1,2-diamine (23.2 mmol) in CH2Cl2 (50 ml) was added CDI (4.51 g, 27.8 mmol). The solution was stirred for 20 h, concentrated in vacuo, the resulting residue suspended in 800 ml diethyl ether, washed with 3× 200 ml 1M Na2CO3, 200 ml sat. NaCl, dried on MgSO4, and concentrated in vacuo. Flash chromatography (2.5%→20% MeOH:CH2Cl2) afforded the title compound as a clear oil (79.3 mg, 0.428 mmol, 2%) as well as additional material heavily contaminated with imidazole g). 1H NMR (CDCl3, 400 MHz) δ 1.24 (s, 6H), 2.23 (s, 6H), 2.41 (m, 2H), 3.24 (s, 2H), 3.34 (m, 2H), 4.96 (s, 1H). ESI/APCI (pos) expected for C9H19N3O: 185.15. Found: 186 (MH+).