反应 #11619

反应方程式

Borane tetrahydrofuran

1-(4-Nitrobenzoyl)piperidine

Borane

→

1-(4-nitro-benzyl)-piperidine

收率 87.0%

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

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

实验过程

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.

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