Реакция #2195480

Уравнение реакции

ammonia

dimethylamine hydrochloride

3,4-dioleyloxybenzaldehyde

Sodium borohydride

→

N,N-Dimethyl-3,4-dioleyloxybenzylamine

Растворители

ethanol

Условия реакции

Обработка

1. 1
   workup.STIRRINGto stir at room temperature overnight
2. 2
   ФильтрацияThe reaction mixture was filtered
3. 3
   Промывкаthe solids washed with dichloromethane
4. 4
   СушкаThe filtrate was dried over K2CO3
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated
7. 7
   ДругоеThe resultant oil was purified via flash chromatography (2-10% acetone in dichloromethane, 0.5% TEA gradient)
8. 8
   Другоеto afford 5.81 g (87-+%) of a yellow oil

Методика

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.

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