Reaction #2195480

Reaction equation

ammonia

dimethylamine hydrochloride

3,4-dioleyloxybenzaldehyde

Sodium borohydride

→

N,N-Dimethyl-3,4-dioleyloxybenzylamine

Solvents

ethanol

Conditions

Workup

1. 1
   workup.STIRRINGto stir at room temperature overnight
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Washthe solids washed with dichloromethane
4. 4
   DryingThe filtrate was dried over K2CO3
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   OtherThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)
8. 8
   Otherto afford 5.81 g (87-+%) of a yellow oil

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-dioleyloxybenzaldehyde (6.39 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. Concentrated aqueous ammonia (4 mL) was added slowly to the reaction mixture. The reaction mixture was filtered and the solids washed with dichloromethane. 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 5.81 g (87-+%) of a yellow oil.

Source