Piperidine → 1-(3-Fluoro-4-nitrobenzyl)piperidine

HRID 518765노트

반응식

HRID 518765 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CC(O)=O.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

7

반응물 4

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 38081203-Fluoro-4-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 667285141-(3-Fluoro-4-nitrobenzyl)piperidine수율 58.2%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 3-fluoro-4-nitrobenzaldehyde (4.85 g, 28.7 mmol), piperidine (3.12 mL, 31.5 mmol) and 20 drops of AcOH in DCM was added sodium triacetoxyborohydride (6.69 g, 31.5 mmol), and the resulting suspension was stirred at RT for 30 minutes. The reaction was made basic with 2N aqueous NaOH, and extracted with DCM. The organic layer was washed with brine and was dried over sodium sulfate, filtered and concentrated in vacuo to yield a red oil. The residual oil was purified via MPLC, eluting with a gradient of 0-100% EtOAc in hexane to yield 1-(3-fluoro-4-nitrobenzyl)piperidine (3.98 g, 16.70 mmol, 58.2% yield) as an orange oil.

후처리

  1. extractionextracted with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a red oil
  7. customThe residual oil was purified via MPLC
  8. washeluting with a gradient of 0-100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-309246382b44426bbb1cf008a67d8c61
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115127B2

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