Trimethyl orthoformate → HCID 15965417, compound

Temperature

-20 °C

3.94 g (0.03 mol, 1.0 equivalent) of 4-cyanobenzaldehyde was charged in a 300 ml four-necked flask, and dissolved in 60 ml of methanol. 9.55 g (0.09 mol, 3.0 equivalents) of trimethyl orthoformate was added dropwise therein at room temperature, and the mixture was then cooled to −20° C. 5.17 g (0.03 mol, 1.0 equivalent) of 4-dipropylaminobutylamine (4) was added dropwise therein, the mixture was stirred for one hour and further stirred at room temperature for three hours. After confirming the disappearance of the raw material, the mixture was again cooled to −20° C. 1.36 g (0.036 mol, 1.2 equivalents) of sodium borohydride was added dropwise therein, and the mixture was stirred for two hours. The reaction solution was added into 250 ml of water and extracted with 120 ml of chloroform. The chloroform layer was washed with 150 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 8.58 g of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a) as a colorless oily substance (yield: 99%, GC: 96.7%).

1. stirringfurther stirred at room temperature for three hours
2. temperaturethe mixture was again cooled to −20° C
3. stirringthe mixture was stirred for two hours
4. extractionextracted with 120 ml of chloroform
5. washThe chloroform layer was washed with 150 ml of a saturated sodium chloride aqueous solution
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated

ORD record

ord-d8af156442294bf29077b991ac086335

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977512B2