Borane → 1-(4-Nitrobenzyl)piperidine

HRID 11523

반응식

HRID 11523 반응식
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].B.B.O1CCCC1>O1CCCC1>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 6331BoraneHCID 2254681-(4-Nitrobenzoyl)piperidineHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 7835411-(4-Nitrobenzyl)piperidine수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

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.

후처리

  1. additionslowly added dropwise to a 0° C.
  2. temperatureto warm to room temperature
  3. temperatureis subsequently heated to 60° C.
  4. temperatureThe reaction mixture is maintained at 60° C. overnight
  5. temperatureis cooled to room temperature
  6. customquenched with the addition of concentrated HCl (added until gas evolution stops)
  7. customThe quenched reaction mixture
  8. extractionis then extracted with ethyl acetate and water
  9. customThe organic layer is separated
  10. concentrationconcentrated in vacuo, while the aqueous layer
  11. customis separated
  12. additionmade basic with the addition of aqueous 1M NaOH
  13. extractionThe basic aqueous layer is then extracted with ethyl acetate
  14. extractionthe ethyl acetate layer from this extraction
  15. concentrationis concentrated in vacuo
  16. customThe solids isolated from both concentrated ethyl acetate layers

출처 및 근거

ORD 기록
ord-84c0540ea44042d38bfeda88949d5104
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098236B2

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