반응 #792141

반응 방정식

sodium cyanoborohydride

acetic acid

1-(indan-2-yl)ethanone

cyclopropylamine

→

N-[1-(indan-2-yl)ethyl]cyclopropanamine

수율 28.0%

용매

methanol

반응 조건

후처리

1. 1
   온도at reflux
2. 2
   workup.STIRRINGthe reaction mixture is further stirred for 2 hrs
3. 3
   온도at reflux
4. 4
   기타The cooled reaction mixture
5. 5
   여과is then filtered over a cake of diatomaceous earth
6. 6
   세척The cake is washed twice by 80 ml of methanol
7. 7
   농축the combined methanolic extracts are concentrated under vacuum
8. 8
   workup.ADDITION100 ml of water are then added to the residue
9. 9
   추출The watery layer is extracted with 300 ml of ethyl acetate
10. 10
    세척The organic layer is washed twice by brine
11. 11
    여과filtered over a phase separator paper
12. 12
    기타to yield after concentration 5 g of a yellow oil

실험 절차

To a cooled solution of 3.5 g (21.8 mmol) of 1-(indan-2-yl)ethanone in 100 ml of methanol, are added 10 g of 3 Å molecular sieves and 2.3 g (40.2 mmol) of cyclopropylamine followed by a slow addition of 2.87 ml (50.2 mmol) of acetic acid. The reaction mixture is stirred for 2.5 hrs at reflux. The reaction mixture is then cooled to 0° C. and 1.9 g (30 mmol) of sodium cyanoborohydride are slowly added and the reaction mixture is further stirred for 2 hrs at reflux. The cooled reaction mixture is then filtered over a cake of diatomaceous earth. The cake is washed twice by 80 ml of methanol and the combined methanolic extracts are concentrated under vacuum. 100 ml of water are then added to the residue and the pH is ajusted to 12 with a 0.5 N solution of sodium hydroxyde. The watery layer is extracted with 300 ml of ethyl acetate. The organic layer is washed twice by brine and filtered over a phase separator paper to yield after concentration 5 g of a yellow oil. Column chromatography on silica gel (gradient heptane/ethyl acetate) yields 1.2 g (28% yield) of N-[1-(indan-2-yl)ethyl]cyclopropanamine as a colourless oil (M+H =202).

출처