Sodium Hydroxide → N,N-dipropylbutane-1,4-diamine

30 g (0.178 mol) of 4-dipropylaminobutyronitrile (3) was charged in a 500 ml three-necked flask, 150 ml of ethanol and 90 ml of a 1N sodium hydroxide aqueous solution was added thereto, and the mixture was stirred. 3.0 g of(10 wt %) the Raney nickel prepared in Example 1 was slowly added to the solution. After replacing the atmosphere in the flask with nitrogen and then with hydrogen, the mixture was allowed to react at room temperature for seven days with stirring while using a hydrogen balloon. After confirming that the raw material content had decreased to 1% or less by GC, the reaction solution was filtered through celite and washed with 400 ml of ethanol. After concentrating the filtrate, the residue was dissolved in 400 ml of chloroform and extracted with 200 ml of water. The chloroform layer was washed with 400 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 27.8 g of a colorless oily substance (yield: 90%). The resulting substance was distilled under reduced pressure to obtain 20.5 g of 4-dipropylaminobutylamine (4) (yield: 66.7%, GC: 99%).

1. customto react at room temperature for seven days
2. stirringwith stirring
3. filtrationthe reaction solution was filtered through celite
4. washwashed with 400 ml of ethanol
5. concentrationAfter concentrating the filtrate
6. dissolutionthe residue was dissolved in 400 ml of chloroform
7. extractionextracted with 200 ml of water
8. washThe chloroform layer was washed with 400 ml of a saturated sodium chloride aqueous solution
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customobtaining 27.8 g of a colorless oily substance (yield: 90%)
12. distillationThe resulting substance was distilled under reduced pressure

ORD record

ord-4fd8aec6d83e476fa2dcbee56c66aa91

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977512B2