Réaction #11619

Équation de réaction

Borane tetrahydrofuran

1-(4-Nitrobenzoyl)piperidine

Borane

→

1-(4-nitro-benzyl)-piperidine

Rendement 87.0%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source