These common heterocyclic compound, 13989-82-7, name is 4-(Dimethylamino)butanenitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 13989-82-7
4-(Dimethylamino)butyronitrile (4.4 g) was dissolved in tetrahydrofuran (40 mL), and a 1 mol/L borane/tetrahydrofuran solution (40 mL) was added dropwise under ice-cooling. After the completion of the reaction, water was added to the reaction solution. The mixture was extracted with ethyl acetate, washed with saturated brine and dried over magnesium sulfate. The solvent was concentrated, and the obtained residue was purified by silica gel column chromatography. A hexane:ethyl acetate=1:1 effluent fraction was concentrated to give (4-(dimethylamino)butyronitrile-N1)trihydroboron (2.8 g). The reaction was carried out in the same manner as in Example 82 using N,N-dimethyl-2,3-dimethylbenzamide (3.9 g) and (4-(dimethylamino)butyronitrile-N1)trihydroboron to give (3-(3-(dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one-N1)trihydroboron (2.0 g). (3-(3-(Dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one-N1)trihydroboron (2.0 g) was dissolved in acetone (20 mL), and conc. hydrochloric acid (1 mL) was added at room temperature. After the completion of the reaction, the solvent was concentrated. Toluene was added to the obtained residue, and the mixture was extracted with water. Potassium carbonate was added to basify the aqueous layer, and the mixture was extracted with chloroform and dried over magnesium sulfate. The solvent was concentrated, and the obtained residue was purified by silica gel column chromatography (NH silica gel, Fuji Silysia Chemical Ltd.). A chloroform effluent fraction was concentrated, and diisopropyl ether was added to the obtained residue. The precipitated crystals were collected by filtration to give 3-(3-(dimethylamino)propyl)-5-methyl-2H-isoquinolin-1-one (1.5 g). melting point: 105-106C.1H-NMR(CDCl3) delta: 1.79-1.89(2H,m), 2.34(6H,s), 2.39(2H,t,J=6Hz), 2.49(3H,s), 2.69(2H,t,J=6Hz), 6.34(1H,s), 7.31(1H,t,J=8Hz), 7.42(1H,dd,J=1Hz,7Hz), 8.23(1H,d,J=8Hz), 11.37(1H,brs).
The synthetic route of 4-(Dimethylamino)butanenitrile has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Mitsubishi Pharma Corporation; EP1396488; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts