Reaction #2075689

Reaction equation

ammonia

dimethylamine hydrochloride

3,4-dilinoleyloxybenzaldehyde

Sodium borohydride

→

yellow oil

Yield 74.4%

N,N-Dimethyl-3,4-dilinoleyloxybenzylamine

Yield 74.4%

Solvents

dichloromethane

ethanol

Conditions

Workup

1. 1
   workup.STIRRINGto stir at room temperature overnight
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   DryingThe filtrate was dried over K2CO3
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)

Procedure

To a solution of triethylamineamine (2.0 mL, 14 mmol) in ethanol (20 mL) was added dimethylamine hydrochloride (1.63 g, 20 mmol), titanium tetraisopropoxide (5.96 mL, 20 mmol) and 3,4-dilinoleyloxybenzaldehyde (6.35 g, 10 mmol). The mixture was allowed to stir under argon for 10 h at room temperature. Sodium borohydride (0.57 g, 15 mmol) was added to the reaction mixture which was then allowed to stir at room temperature overnight. 6N Aqueous ammonia (30 mL), was added slowly to the reaction mixture followed by dichloromethane. The reaction mixture was filtered. The filtrate was dried over K2CO3, filtered and concentrated. The resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient) to afford 4.94 g (74%) of a yellow oil.

Source