Реакция #1052425

Уравнение реакции

sodium cyanoborohydride

acetic acid

(±) cis 2-amino-1-(3,4dichlorophenoxy)indane

formaldehyde

→

title compound

(±) cis 1-(3,4-Dichlorophenoxy)-2-dimethylaminoindane Hydrochloride

Растворители

diethyl ether

acetonitrile

Условия реакции

Обработка

1. 1
   Температураwhile maintaining the pH at 5-7
2. 2
   Промывкаwashed with 1M sodium hydroxide
3. 3
   ДругоеThe organic layer was dried over Na2 SO4
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеPassage through a short column of neutral alumina eluting with 0.5-1% ethanol in chloroform afforded a colourless oil which
6. 6
   Другоеrecrystallised

Методика

A solution of (±) cis 2-amino-1-(3,4dichlorophenoxy)indane (0.88 g, 3.0 mmol) in acetonitrile (40 ml) was treated with formaldehyde (2 ml of a 37% aqueous solution, 26 mmol) followed by sodium cyanoborohydride (0.38 g, 6.0 mmol). The mixture was stirred at room temperature for 6 days while maintaining the pH at 5-7 by the addition of glacial acetic acid. The reaction mixture was diluted with diethyl ether and washed with 1M sodium hydroxide followed by brine. The organic layer was dried over Na2 SO4 and concentrated in vacuo. Passage through a short column of neutral alumina eluting with 0.5-1% ethanol in chloroform afforded a colourless oil which was converted into the hydrochloride salt and recrystallised to give the title compound as a colourless solid (0.6 g), m.p. 219°-220° C. (from methanol/ethyl acetate/diethyl ether).

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