Ethyl Acrylate → HCID 9841084, compound

HRID 1840967Notes

Reaction equation

HRID 1840967 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:7]1)[CH3:2].[C:21]([O:25]CC)(=[O:24])[CH:22]=[CH2:23]>C(O)C>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]2[CH2:16][CH2:17][N:18]([CH2:23][CH2:22][C:21]([OH:25])=[O:24])[CH2:19][CH2:20]2)=[CH:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 99036001-(2-ethoxyethyl)-3-piperidin-4-yl-1H-indole

Product 1

HCID 9841084HCID 9841084, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.5 g (1.84 mmol) of 4-[1-(2-ethoxy-ethyl)-indol-3-yl)-piperidine prepared as in Example 152 (part D) in 6 mL of ethyl alcohol, 0.240 g (2.4 mmol) of ethyl acrylate were added. The mixture was refluxed for 18 hours and the solvent was removed under reduced pressure. The residue was extracted between water and ethyl acetate. The crude product obtained after removing the solvent was dissolved with 3 mL of ethyl alcohol and 2 mL of a 2N aqueous sodium hydroxide solution were added. The mixture was stirred at room temperature for 18 hours and then neutralised with HCl 6N. After extraction with chloroform and removal of the solvent, 0.420 g (67%) of a yellow oil were isolated.

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed for 18 hours
  3. customthe solvent was removed under reduced pressure
  4. extractionThe residue was extracted between water and ethyl acetate
  5. customThe crude product obtained
  6. customafter removing the solvent
  7. dissolutionwas dissolved with 3 mL of ethyl alcohol and 2 mL of a 2N aqueous sodium hydroxide solution
  8. additionwere added
  9. extractionAfter extraction
  10. customwith chloroform and removal of the solvent

Sources & evidence

ORD record
ord-2b4ca74d7b4142a0a9cb72cd66b8658c
Source dataset
uspto-grants-2004_01
Patent number
US06683096B2

Reaction notes

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