Benzene → HCID 53891048, compound

HRID 2290728Notes

Reaction equation

HRID 2290728 reaction equation
C1C=CC=CC=1.[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[OH:16])[CH2:9]1.[CH2:23]=[C:24]1[O:28][C:26](=[O:27])[CH2:25]1>C(N(CC)CC)C>[C:26]([O:16][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][N:10]1[CH2:11][CH2:12][CH2:13][CH:8]([CH3:7])[CH2:9]1)(=[O:27])[CH2:25][C:24]([CH3:23])=[O:28]

Participants

5

Reactant 3

HCID 241BenzeneHCID 12661DiketeneHCID 20230106HCID 20230106, compound

Product 1

HCID 53891048HCID 53891048, compoundYield 106.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 100 ml of benzene are added 9.5 g of 2-(3-methyl piperidino)-1-phenylethanol having a melting point of 70° C., 5 g of diketene and 0.1 ml of triethylamine, and the mixture is refluxed under heating for two hours. The reaction mixture is concentrated under reduced pressure to give 14 g of 2-(3-methylpiperidino)-1-phenylethyl acetoacetate as oily substance. To 150 ml of isopropanol are added 14 g of 2-(3-methylpiperidino)-1-phenylethyl acetoacetate, 6.5 g of m-nitrobenzaldehyde and 5 g of methyl β-aminocrotonate, and the mixture is refluxed under heating for 15 hours. The reaction mixture is concentrated under reduced pressure and the oily residue is dissolved in ethyl acetate. The ethyl acetate layer is washed with 1N-hydrochlroic acid, potassium carbonate and water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The oily residue (25 g) is purified by column chromatography. The eluate is concentrated and the residue is dissolved in acetone, whereupon an ethanol solution of hydrogen chloride is added to crystallize. The precipitated crystals are collected by filtration and recrystallized from ethanol to give 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-[2-(3-methylpiperidino)-1-phenyl]ester in the form of hydrochloride as crystals melting at 225° C.-226° C. (decomposition).

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for two hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure

Sources & evidence

ORD record
ord-48debb8195144b9783fd421fcde3f9f8
Source dataset
uspto-grants-1986_10
Patent number
US04618607

Reaction notes

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