2-Nitrobenzaldehyde → Piperidine

HRID 1164585Notes

Reaction equation

HRID 1164585 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15]>C1C=CC=CC=1>[NH:1]1[CH2:4][CH2:5][CH2:8][CH2:9][CH2:10]1.[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[C:13]([C:14]([CH3:16])=[O:15])[C:12]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:17])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 12237326Butanoic acid, 3-oxo-, 2-phenoxyethyl ester

Product 2

HCID 8082PiperidineHCID 53638503HCID 53638503, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Starting from a mixture of 2-nitrobenzaldehyde (3.02 g), 2-phenoxyethyl acetoacetate (4.44 g), piperidine (272.5 mg) in benzene (10.8 ml) was obtained an oil (8.0 g) of 2-phenoxyethyl 2-(2-nitrobenzylidene)acetoacetate. Thus obtained oil was treated with ethyl 3-amino-4,4-diethoxycrotonate (4.34 g) to given an oil of 2-phenoxyethyl 2-methyl-4-(2-nitrophenyl)-5-ethoxycarbonyl-6-diethoxymethyl-1,4-dihydropyridine-3-carboxylate.

Sources & evidence

ORD record
ord-c32a210f6abf408ba2ebc38294f3305c
Source dataset
uspto-grants-1983_01
Patent number
US04370334

Reaction notes

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