2-Indanone → HCID 58107514, compound

HRID 873677Notes

Reaction equation

HRID 873677 reaction equation
CO[C:3](=O)[CH2:4][CH2:5][NH:6][CH2:7][CH3:8].[CH2:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=[O:19]>C1(C)C=CC=CC=1>[CH2:7]([N:6]1[C:11](=[O:19])[CH2:10][CH2:18][C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=3[CH2:4][C:5]1=2)[CH3:8]

Participants

4

Reactant 2

HCID 119832-IndanoneHCID 76973Methyl N-ethyl-beta-alaninate

Product 1

HCID 58107514HCID 58107514, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Ethylamino-propionic acid methyl ester (2.41 g, 18.4 mmol) is added to a solution of 2-indanone (2.3 g, 17.33 mmol) in toluene (27 mL), and the reaction is brought to reflux for 2 hours. Toluene is removed in vacuo and the residue is dissolved in ethylene glycol (23 mL) and the resulting solution is heated to reflux for 8 hours. The reaction is allowed to cool to ambient temperature and is poured over water and extracted with dichloromethane. The organic phase is dried over magnesium sulfate and concentrated in vacuo to afford the crude title compound. The crude product is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-100%) affording 1 g (27% yield) of the title compound. MS (m/z): 213.3 (M+1).

Workup

  1. temperatureto reflux for 2 hours
  2. customToluene is removed in vacuo
  3. dissolutionthe residue is dissolved in ethylene glycol (23 mL)
  4. temperaturethe resulting solution is heated
  5. temperatureto reflux for 8 hours
  6. additionis poured over water
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic phase is dried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto afford the crude title compound
  11. customThe crude product is purified by silica gel chromatography (gradient of ethyl acetate in hexanes 10-100%)

Sources & evidence

ORD record
ord-54bbd43bfcc944a489deded75ffc4c94
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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