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

HRID 437640Notes

Reaction equation

HRID 437640 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([N:8]1[CH2:10][CH2:9]1)=[O:7])([O-:3])=[O:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:28])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C1C=CC=CC=1>CO>[ClH:15].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([OH:28])[CH2:23][CH2:24][N:25]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]3[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:26][CH2:27]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 382824-(4-Chlorophenyl)-4-hydroxypiperidineHCID 214289511-(2-Nitrobenzoyl)aziridine

Product 1

HCID 21428974N-{2-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]ethyl}-2-nitrobenzamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7.6 parts of 1-(2-nitrobenzoyl)aziridine, 8.46 parts of 4-(4-chlorophenyl)-4-piperidinol, 43.2 parts of benzene and 6.4 parts of methanol is stirred and refluxed for 1.50 hours. The reaction mixture is cooled and the product is extracted with trichloromethane. The extract is washed three times with water, dried, filtered and evaporated. The residue is converted into the hydrochloride salt in 2-propanone. The salt is filtered off and crystallized from a mixture of ethanol and 2,2'-oxybispropane. The product is filtered off and dried, yielding 6parts of N-{2-[4-(4-chlorophenyl)-4- hydroxy-1-piperidinyl]ethyl}-2-nitrobenzamide hydrochloride; mp. 174.1° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionthe product is extracted with trichloromethane
  4. washThe extract is washed three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt is filtered off
  9. customcrystallized from a mixture of ethanol and 2,2'-oxybispropane
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-3e25ca36265c40bf95d834fea3b58e91
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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