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

HRID 437641Notes

Reaction equation

HRID 437641 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5d5cf8e2d3474fd6aa926ce897778cee
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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