4-Bromobenzaldehyde → HCID 16117294, compound

Participants

Reaction Conditions

Reaction Steps

0.40 g (1.39 mmol) of 4-[(4-dipropylaminobutyl)amino]methylbenzonitrile (2a), 8.0 ml of ethanol, and 514 mg (2.78 mmol, 2.0 equivalents) of 4-bromobenzaldehyde were charged in a 50 ml recovery flask under a nitrogen stream. The mixture was then cooled to 0° C. After the addition of 0.707 g (3.34 mmol, 2.4 equivalents) of sodium triacetoxyborohydride, the mixture was stirred for 22 hours. After confirming the disappearance of the raw material by TLC, the reaction solution was added to 50 ml of a saturated sodium bicarbonate aqueous solution, and extracted twice with 50 ml of chloroform. The chloroform layer was washed with 100 ml of a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (Chromatorex NH (manufactured by FujiSilysia Chemical Ltd.), n-hexane:ethyl acetate=3:1), thereby obtaining 0.508 g of 4-{[(4-bromobenzyl)-(4-dipropylaminobutyl)amino]methyl}benzonitrile (15) as a light yellow oily substance (yield: 80.0%). [HPLC: 96.2% (HPLC measurement conditions B)]

Provenance & Evidence