Reacción #2195480

Ecuación de reacción

ammonia

dimethylamine hydrochloride

3,4-dioleyloxybenzaldehyde

Sodium borohydride

→

N,N-Dimethyl-3,4-dioleyloxybenzylamine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGto stir at room temperature overnight
2. 2
   FiltraciónThe reaction mixture was filtered
3. 3
   Lavadothe solids washed with dichloromethane
4. 4
   SecadoThe filtrate was dried over K2CO3
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)
8. 8
   Otroto afford 5.81 g (87-+%) of a yellow oil

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-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.

Fuente