Réaction #2075689

Équation de réaction

ammonia

dimethylamine hydrochloride

3,4-dilinoleyloxybenzaldehyde

Sodium borohydride

→

yellow oil

Rendement 74.4%

N,N-Dimethyl-3,4-dilinoleyloxybenzylamine

Rendement 74.4%

Solvants

dichloromethane

ethanol

Conditions de réaction

Traitement

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

Mode opératoire

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