Benzene → N--{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-nitrobenzamide

HRID 437641노트

반응식

HRID 437641 반응식
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[C:4]([N+:13]([O-:15])=[O:14])[CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([OH:29])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C1C=CC=CC=1>CO>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2([OH:29])[CH2:24][CH2:25][N:26]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]3[CH:11]=[CH:12][C:2]([F:1])=[CH:3][C:4]=3[N+:13]([O-:15])=[O:14])[CH2:27][CH2:28]2)=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 241BenzeneHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 214288531-(4-Fluoro-2-nitrobenzoyl)aziridine

생성물 1

HCID 21428896N--{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-nitrobenzamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 15 parts of 1-(4-fluoro-2-nitrobenzoyl)-aziridine, 11 parts of 4-(4-chlorophenyl)-4-piperidinol, 55.8 parts of benzene and 8.8 parts of methanol is stirred and refluxed for 1.50 hours. After stirring is continued overnight at room temperature, the reaction mixture is evaporated. The residue is dissolved in trichloromethane. The solution is washed with water and 8 parts of methanol are added. The whole is stirred for 10 minutes with silica gel. The latter is filtered off and the filtrate is evaporated. The residue is triturated with 2,2'-oxybis propane. The precipitated product is filtered off and crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 9.5 parts of N-{2-[4-(4-chlorophenyl)-4- hydroxy-1-piperidinyl]ethyl}-4-fluoro-2-nitrobenzamide; mp. 144.3° C.

후처리

  1. temperaturerefluxed for 1.50 hours
  2. stirringAfter stirring
  3. customthe reaction mixture is evaporated
  4. dissolutionThe residue is dissolved in trichloromethane
  5. washThe solution is washed with water and 8 parts of methanol
  6. additionare added
  7. stirringThe whole is stirred for 10 minutes with silica gel
  8. filtrationThe latter is filtered off
  9. customthe filtrate is evaporated
  10. customThe residue is triturated with 2,2'-oxybis propane
  11. filtrationThe precipitated product is filtered off
  12. customcrystallized from 4-methyl-2-pentanone
  13. filtrationThe product is filtered off
  14. customdried

출처 및 근거

ORD 기록
ord-5d5cf8e2d3474fd6aa926ce897778cee
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031226

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