반응 #65920

반응 방정식

sodium hydroxide

2-cycloheptylcarbamoylmethylfluorene

methanol

hydrochloric acid

→

2-cycloheptylaminoethylfluorene

수율 66.0%

용매

chloroform

tetrahydrofuran

chloroform

반응 조건

후처리

1. 1
   workup.ADDITIONfollowed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-
2. 2
   온도cooling
3. 3
   workup.ADDITIONwas added with ice-
4. 4
   온도cooling
5. 5
   온도cooling
6. 6
   온도The mixture was refluxed again for 30 minutes
7. 7
   온도The reaction mixture was then cooled with ice
8. 8
   여과the resulting solid was recovered by filtration
9. 9
   세척washed with ether
10. 10
    기타The solid matter thus obtained
11. 11
    기타dried
12. 12
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

실험 절차

In dry tetrahydrofuran (30 ml) was dissolved 2-cycloheptylcarbamoylmethylfluorene (1.9 g) followed by dropwise addition of borane-methyl sulfide complex (1.8 ml) with ice-cooling. The mixture was then refluxed for 4 hrs, at the end of which time methanol (0.72 ml) was added with ice-cooling. The mixture was stirred at room temperature for 30 minutes, followed by addition of concentrated hydrochloric acid (1.8 ml) with ice-cooling. The mixture was refluxed again for 30 minutes. The reaction mixture was then cooled with ice and the resulting solid was recovered by filtration and washed with ether. The solid matter thus obtained was dissolved in chloroform and the solution was alkalinized with aqueous sodium hydroxide solution. The chloroform layer was taken and dried and the solvent was distilled off under reduced pressure to give 2-cycloheptylaminoethylfluorene (1.2 g).

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