Nitric Acid → 4-(4-Nitrophenyl)piperidine

HRID 409678

반응식

HRID 409678 반응식
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[C:10]1([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(O)=O.[Na+]>CC(O)=O>[N+:6]([C:13]1[CH:12]=[CH:11][C:10]([CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)=[CH:15][CH:14]=1)([O-:9])=[O:7]

참가 물질

6

반응물 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2회HCID 698734-PhenylpiperidineHCID 516892Sodium Bicarbonate

생성물 1

HCID 159258174-(4-Nitrophenyl)piperidine

시약·촉매·용매 1

HCID 176Acetic Acid용매3회

실험 절차

A solution of conc. H2SO4 (2.65 mL) in AcOH (40 mL) and a solution of conc. HNO3 (2.1 mL) in AcOH (20 mL) are added sequentially and dropwise to a solution of 4-phenylpiperidine in AcOH (40 mL), maintaining the temperature below 20° C. Then, conc. H2SO4 (40 mL) is added (no cooling applied; internal temperature reaches 60° C.). The reaction mixture is allowed to cool to RT, poured onto ice/water (100 g), neutralized by addition of solid NaHCO3 (150 g), and extracted with DCM. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by trituration in Et2O to afford the title compound as a yellow solid. ESI-MS: 207.1 [MH]+; tR=2.42 min (system 1).

후처리

  1. temperaturemaintaining the temperature below 20° C
  2. customreaches 60° C.
  3. additionpoured onto ice/water (100 g)
  4. extractionextracted with DCM
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by trituration in Et2O

출처 및 근거

ORD 기록
ord-5f6a682a90d44a2ab2ace0188ad48486
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759517B2

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