Ethyl Acrylate → HCID 9841126, compound

HRID 2371715Notes

Reaction equation

HRID 2371715 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:22]([O:26]CC)(=[O:25])[CH:23]=[CH2:24].[OH-].[Na+]>CO>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:17][CH2:18][N:19]([CH2:24][CH2:23][C:22]([OH:26])=[O:25])[CH2:20][CH2:21]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 14798Sodium HydroxideHCID 1597184-(5H-Dibenzo(a,d)cyclohepten-5-ylidene)piperidine

Product 1

HCID 9841126HCID 9841126, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 146 g of 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, 73.0 g of ethyl acrylate and 500 ml of methanol was refluxed for 1 hr and then 675 ml of 2N sodium hydroxide aqueous solution was added to the reaction mixture. The reaction mixture was refluxed for 1 hr and concentrated. Water was added to the residue and adjusted to pH 4 with hydrochloric acid. The precipitate was collected by filtration to give 200 g of colorless crystals, which were recrystallized from a mixture of water and N,N-dimethylformamide to give 198 g of colorless crystals. This compound was identified by comparing its mp, IR spectrum and NMR spectrum with those of the compound of Example 21.

Workup

  1. temperaturewas refluxed for 1 hr
  2. temperatureThe reaction mixture was refluxed for 1 hr
  3. concentrationconcentrated
  4. additionWater was added to the residue
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-23b7adc41d37426e849defad0b9ba23e
Source dataset
uspto-grants-1992_03
Patent number
US05095022

Reaction notes

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