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Hydrochloric Acid → 1-(2,6-Difluoro-4-nitrophenyl)piperidin-4-one

HRID 1429237
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HRID 1429237 반응식
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:21][CH2:20][C:15]2(OCC[O:16]2)[CH2:14][CH2:13]1.O.Cl>CC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH2:21][CH2:20][C:15](=[O:16])[CH2:14][CH2:13]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

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HCID 313Hydrochloric AcidHCID 962WaterHCID 580319788-(2,6-Difluoro-4-nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

생성물 1

HCID 218781831-(2,6-Difluoro-4-nitrophenyl)piperidin-4-one수율 81%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
50 °C

실험 절차

The crude 8-(2,6-difluoro-4-nitrophenyl)-1,4-dioxa-8-azaspiro[4.5]decane from the preceding procedure was dissolved in 4:1 acetone:water (100 mL). Concentrated HCl (5 mL) was added, and the resulting mixture was stirred at 50° C. for 8 hours and then cooled to room temperature. The mixture was concentrated in vacuo to approximately 20 mL, which was carefully added to concentrated aq. NaHCO3 (100 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was triturated with Et2O and hexanes to give a bright-yellow solid that was collected and dried to provide the title compound (7.13 g, 81%).

후처리

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated in vacuo to approximately 20 mL, which
  3. additionwas carefully added to concentrated aq. NaHCO3 (100 mL)
  4. extractionextracted with EtOAc (2×100 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was triturated with Et2O and hexanes
  9. customto give a bright-yellow solid
  10. customthat was collected
  11. customdried

출처 및 근거

ORD 기록
ord-988c24fef22a420dac0c523074b449bb
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08937150B2

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