Reaktion #11619

Reaktionsgleichung

Borane tetrahydrofuran

1-(4-Nitrobenzoyl)piperidine

Borane

→

1-(4-nitro-benzyl)-piperidine

Ausbeute 87.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle