Hydrochloric Acid → HCID 22668527, compound

Temperature

65 °C

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 thrice 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.

1. stirringAfter stirring at this temperature for 6 hours
2. temperatureto cool to room temperature
3. extractionextracted thrice with chloroform (3×30 mL)
4. extractionThe basic phase is extracted thrice with chloroform (3×30 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give an orange-red oil, which
8. customis purified by reverse phase high performance liquid chromatography

ORD record

ord-ecd76990e06c43d8aae63040f47f91b0

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07713994B2