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

HRID 746248
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04603135

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes