Reacción #2195481

Ecuación de reacción

ammonia

dimethylamine hydrochloride

3,4-dilinoleyloxybenzaldehyde

Sodium borohydride

→

yellow oil

Rendimiento 74.4%

N,N-Dimethyl-3,4-dilinoleyloxybenzylamine

Rendimiento 74.4%

Disolventes

dichloromethane

ethanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente