Benzene → HCID 13909610, compound

HRID 2290727Notes

Reaction equation

HRID 2290727 reaction equation
C1C=CC=CC=1.[C:7]1([CH:13]([OH:21])[CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:22]=[C:23]1[O:27][C:25](=[O:26])[CH2:24]1>C(N(CC)CC)C>[C:25]([O:21][CH:13]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)(=[O:26])[CH2:24][C:23]([CH3:22])=[O:27]

Participants

5

Reactant 3

HCID 241BenzeneHCID 12661DiketeneHCID 172021-phenyl-2-piperidin-1-ylethanol

Product 1

HCID 13909610HCID 13909610, compoundYield 106.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 130 ml of benzene are added 14.7 g of 1-phenyl-2-piperidinoethanol, 7.1 g of diketene and 1 ml of triethylamine. The mixture is refluxed under heating for three hours. The reaction mixture is concentrated under reduced pressure to give 22 g of 1-phenyl-2-piperidinoethyl acetoacetate. A mixture of 22 of 1-phenyl-2-piperidinoethyl acetoacetate, 10.6 g of m-nitrobenzaldehyde and 12.7 g of (2-furyl)methyl β-aminocrotonate in 130 ml of isopropanol is refluxed under heating for 12 hours. The reaction mixture is concentrated under reduced pressure. To the viscous jelly-like oily substance thus obtaned is added an ethanol solution of hydrogen chloride and then the mixture is concentrated. The viscous jelly-like residue is crystallized from a mixture solvent of acetone-ether. The precipitated crystals are collected by filtration, and recrystallized from a mixture solvent of acetone-methanol to give α-diastereoisomer of 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(2-furyl)methylester-5-(1-phenyl-2-piperidinoethyl)ester in the form of hydrochloride as yellow crystals melting at 219°-221° C. (decomposition).

Workup

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

Sources & evidence

ORD record
ord-12001bcee31f412586400327f7988157
Source dataset
uspto-grants-1986_10
Patent number
US04618607

Reaction notes

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