l suction flask about 28 4 g valeraldehyde u02dc 0 34 mol and then u02dc 37 8 g n hexyl n methylamine u02dc 0 33 mol were mixed into the thf about 100 g of sodium triacetoxyborohydride powder was then added in u02dc 5 10 g increments to the solution during the addition vigorous stirring was used to ensure that the powder clumped as little as possible at the bottom of the flask thereby preventing efficient mixing of the suspension after each addition of the sodium triacetoxyborohydride powder adequate time was provided to form a relatively uniform slurry before the next addition of the powder once all of the powder had been added the nitrogen flow was then turned on after overnight mixing u02dc 8 16 hours the product was worked up by quenching the suspension with the slow addition of u02dc 275 g of a u02dc 24 mass koh aqueous solution the product was then extracted from the resultant solution with pentane the organic fraction was then collected with a separatory funnel and dried with anhydrous magnesium sulfate the amine product was then isolated by rotary evaporation of the thf and pentane solvents under gradually reduced pressure down to u02dc 50 torr to yield u02dc 60 6 g of amine product.