HCID 15965417, compound → HCID 59850548, compound

Participants

Reaction Steps

4.0 g (13.91 mmol, 1.0 equivalent) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a) and 24 ml of methanol were charged in a 100 ml three-necked flask. 400 mg (10 wt %) of the Raney nickel prepared in Example 1 was then slowly added to the mixture. After the addition of 2.58 g (13.35 mmol, 0.96 equivalents) of a 28% sodium methoxide/methanol solution, the atmosphere in the flask was replaced with nitrogen and then with hydrogen. The mixture was then stirred at room temperature for five days using a hydrogen balloon. After completion of the reaction, the reaction solution was filtered through celite. After concentration, the resulting residue was added to 50 ml of water. The product was extracted with 100 ml of chloroform three times. The chloroform layer was washed twice with 100 ml of water, dried over anhydrous sodium sulfate, and concentrated, thereby obtaining 4.0 g of 4-[(4-dipropylaminobutyl)amino]methylbenzylamine (5a) as a colorless oily substance (yield: 99%, GC: 96.0%).

Provenance & Evidence