Benzene → 2-(4-Benzhydryl-1-piperazinyl)ethyl 2-(3-nitrobenzylidene)acetoacetate

HRID 746238Notes

Reaction equation

HRID 746238 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].C1C=CC=CC=1.N1CCCCC1>O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:25][CH2:26]1)=[O:17])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 11740518Butanoic acid, 3-oxo-, 2-[4-(diphenylmethyl)-1-piperazinyl]ethyl ester

Product 1

HCID 541101302-(4-Benzhydryl-1-piperazinyl)ethyl 2-(3-nitrobenzylidene)acetoacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of m-nitrobenzaldehyde (1.67 g), 2-(4-benzhydryl-1-piperazinyl)ethyl acetoacetate (4.20 g), benzene (40 ml) and piperidine (0.05 g) was refluxed for 4 hours, during which time the water produced was removed using a Dean-Stark trap. The mixture was washed with water and dried (MgSO4). The solvent was then distilled off and the residue was purified by column chromatography on silica gel (100 g) [eluent: ethyl ether-ethyl acetate (10:1, v/v)] to give 2-(4-benzhydryl-1-piperazinyl)ethyl 2-(3-nitrobenzylidene)acetoacetate as an oil. Yield 4.37 g.

Workup

  1. customproduced
  2. customwas removed
  3. washThe mixture was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was then distilled off
  6. customthe residue was purified by column chromatography on silica gel (100 g) [eluent

Sources & evidence

ORD record
ord-8211de46831d460cb83280e10268f9b7
Source dataset
uspto-grants-1986_07
Patent number
US04603135

Reaction notes

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