Hydrochloric Acid → HCID 22668527, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of potassium hydroxide (1.4 g, 25 mmol) in dimethylsulfoxide (13 mL) is added N,N,N′-trimethyl-1,3-propanediamine (1.8 mL, 12 mmol). While stirring vigorously and while heating to 65° C., 4-fluoronitrobenzene (1.1 mL, 10 mmol) is added dropwise. After stirring at this temperature for 6 hours, the mixture is allowed to cool to room temperature. Water is added and the mixture is acidified to pH 1 with concentrated hydrochloric acid and then extracted 3× with chloroform (3×30 mL). The acidic phase is then basified to pH 11 with 2.5 M sodium hydroxide solution. The basic phase is extracted thrice with chloroform (3×30 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give an orange-red oil, which is purified by reverse phase high performance liquid chromatography to give N,N,N′-trimethyl-N′-(4-nitrophenyl)propane-1,3-diamine as its ditrifluoroacetate salt.

Provenance & Evidence