Nitric Acid → 1-[5-Nitro-2-(4-pyridinylamino)benzoyl]piperidine

HRID 64889노트

반응식

HRID 64889 반응식
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[C:10]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:3][CH:2]=1.[N+:22]([O-])([OH:24])=[O:23]>S(=O)(=O)(O)O>[N+:22]([C:19]1[CH:20]=[CH:21][C:8]([NH:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[C:9]([CH:18]=1)[C:10]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)=[O:11])([O-:24])=[O:23]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 557541-Piperidinyl(2-(4-pyridinylamino)phenyl)methanone

생성물 1

HCID 137124581-[5-Nitro-2-(4-pyridinylamino)benzoyl]piperidine

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매2회

반응 조건

온도
5 °C

실험 절차

To a solution of 20 g of 1-[2-(4-pyridinylamino)benzoyl]piperidine (Example 1b) in 75 ml of sulfuric acid cooled in an ice-salt bath was slowly added a solution of 6.5 ml of concentrated nitric acid in 65 ml of sulfuric acid. The mixture was stirred at 5° C. for four hours and then poured onto ice and allowed to stand overnight. A crystalline acid-addition salt formed which was collected, dissolved in water and converted to the free base by adding sodium bicarbonate. The free base product was extracted with methylene dichloride, the extracts dried over anhydrous sodium sulfate and concentrated, and the residue triturated with ethyl acetate to give 9.3 g of 1-[5-nitro-2-(4-pyridinylamino)benzoyl]piperidine as a yellow powder, m.p. 194°-196° C.(decompn.).

후처리

  1. additionpoured onto ice
  2. waitto stand overnight
  3. customA crystalline acid-addition salt formed which
  4. customwas collected
  5. dissolutiondissolved in water
  6. additionby adding sodium bicarbonate
  7. extractionThe free base product was extracted with methylene dichloride
  8. dry with materialthe extracts dried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customthe residue triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-78d5de1622f44856b761b71c261c66e6
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04610991

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