반응 #11619

반응 방정식

Borane tetrahydrofuran

1-(4-Nitrobenzoyl)piperidine

Borane

→

1-(4-nitro-benzyl)-piperidine

수율 87.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONslowly added dropwise to a 0° C.
2. 2
   온도to warm to room temperature
3. 3
   온도is subsequently heated to 60° C.
4. 4
   온도The reaction mixture is maintained at 60° C. overnight
5. 5
   온도is cooled to room temperature
6. 6
   기타quenched with the addition of concentrated HCl (added until gas evolution stops)
7. 7
   기타The quenched reaction mixture
8. 8
   추출is then extracted with ethyl acetate and water
9. 9
   기타The organic layer is separated
10. 10
    농축concentrated in vacuo, while the aqueous layer
11. 11
    기타is separated
12. 12
    workup.ADDITIONmade basic with the addition of aqueous 1M NaOH
13. 13
    추출The basic aqueous layer is then extracted with ethyl acetate
14. 14
    추출the ethyl acetate layer from this extraction
15. 15
    농축is concentrated in vacuo
16. 16
    기타The solids isolated from both concentrated ethyl acetate layers

실험 절차

1-(4-Nitrobenzoyl)piperidine (0.1125 gms.) is then dissolved in tetrahydrofuran (1 mL) and slowly added dropwise to a 0° C., 1.0 M solution (4 mL) of Borane in tetrahydrofuran. The reaction mixture is maintained at 0° C. for 20 minutes following the completion of the addition to the Borane/tetrahydrofuran solution. The reaction mixture is then allowed to warm to room temperature, and is subsequently heated to 60° C. using an oil bath. The reaction mixture is maintained at 60° C. overnight, then is cooled to room temperature, and quenched with the addition of concentrated HCl (added until gas evolution stops). The quenched reaction mixture is then extracted with ethyl acetate and water. The organic layer is separated, and concentrated in vacuo, while the aqueous layer is separated and made basic with the addition of aqueous 1M NaOH. The basic aqueous layer is then extracted with ethyl acetate and the ethyl acetate layer from this extraction is concentrated in vacuo. The solids isolated from both concentrated ethyl acetate layers are combined to yield 92 mg of 1-(4-nitro-benzyl)-piperidine as a white-yellow solid.

출처