Benzene → 2-(4-Phenylpiperidino)-ethyl 2-(3-nitrobenzylidene)acetoacetate

HRID 746248Notes

Reaction equation

HRID 746248 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][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1.C1C=CC=CC=1>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][CH:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][CH2:26]1)=[O:17])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 74493-NitrobenzaldehydeHCID 8082PiperidineHCID 138611532-(4-Phenylpiperidino)ethyl acetoacetate

Product 1

HCID 539264322-(4-Phenylpiperidino)-ethyl 2-(3-nitrobenzylidene)acetoacetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of m-nitrobenzaldehyde (0.66 g), 2-(4-phenylpiperidino)ethyl acetoacetate (1.2 g), piperidine (0.1 ml) and benzene (20 ml) was refluxed overnight, during which time the water produced was removed azeotropically. The solvent was then distilled off and the residue was chromatographed on silica gel (50 g) [ethyl acetate-hexane (1:1, v/v)] to give 2-(4-phenylpiperidino)-ethyl 2-(3-nitrobenzylidene)acetoacetate as an oil. Yield 0.80 g (45.7%).

Workup

  1. customproduced
  2. customwas removed azeotropically
  3. distillationThe solvent was then distilled off
  4. customthe residue was chromatographed on silica gel (50 g) [ethyl acetate-hexane (1:1

Sources & evidence

ORD record
ord-b989c8e2d49a4d30a6c718b5c48d2aea
Source dataset
uspto-grants-1986_07
Patent number
US04603135

Reaction notes

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