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

HRID 329865Notes

Reaction equation

HRID 329865 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 3

HCID 241BenzeneHCID 74493-NitrobenzaldehydeHCID 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 2

HCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

To a mixture of m-nitrobenzaldehyde (307 mg), 2-(4-benzhydryl-1-piperazinyl)ethyl acetoacetate (668 mg) and benzene (20 ml) was added piperidine (two drops), and the mixture was refluxed for 2 hours under removal of water using a Dean-Stark trap. After cooling, the reaction mixture was washed with water and dried over anhydrous sodium sulfate and the solvent was distilled off to give crude 2-(4-benzhydryl-1-piperazinyl)ethyl 2-(3-nitrobenzylidene)acetoacetate as an oil. NMR(CDCl3) δ: 2.38(3H,s,COCH3), 4.14-4.53(3H,m,--COOCH2CH2 --,>N--CH<), 7.10-8.75(14H,m). This product was submitted to the next reaction step without further purification.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-efa1f1afcf78487db2052d40a5470870
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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