반응 #5046

반응 방정식

Sodium cyanoborohydride

N-(3-chlorophenyl)-1,2-diaminoethane

3-quinuclidinone hydrochloride

acetic acid

→

desired product

수율 3.7%

N-(1-azabicyclo[2.2.2]oct-3-yl)-N'-(3-chlorophenyl)-1,2-diaminoethane

수율 3.7%

용매

methanol

반응 조건

후처리

1. 1
   온도The reaction mixture is refluxed for 10 hours
2. 2
   온도cooled
3. 3
   여과filtered
4. 4
   기타After evaporation to dryness the residue
5. 5
   추출extracted three times with ethyl acetate
6. 6
   세척The organic layer is washed with brine
7. 7
   건조dried over anhydrous sodium sulfate
8. 8
   여과after filtration
9. 9
   기타evaporated to dryness
10. 10
    기타The residue is purified by silica gel flash-chromatography (methylene chloride--methanol--30% ammonium hydroxide, 150:50:5 as eluant)

실험 절차

To a stirred solution of N-(3-chlorophenyl)-1,2-diaminoethane (1 g; 0,00586 moles) in 25 ml of anhydrous methanol kept under nitrogen atmosphere, 3-quinuclidinone hydrochloride (1.01 g, 0.0062? moles) is added. The pH is adjusted to pH 6 by addition of glacial acetic acid. Sodium cyanoborohydride (0.74 g; 0.0117 moles) is added in two portions. The reaction mixture is refluxed for 10 hours, cooled and then filtered. After evaporation to dryness the residue is taken up with water, basified with 20% sodium hydroxide solution and extracted three times with ethyl acetate. The organic layer is washed with brine, dried over anhydrous sodium sulfate and, after filtration, evaporated to dryness. The residue is purified by silica gel flash-chromatography (methylene chloride--methanol--30% ammonium hydroxide, 150:50:5 as eluant) to give the desired product as a clear oil (0.06 g).

출처