7-hydroxy-2-methyl-4H-1-benzopyran-4-one → 7-[3-(4-Benzamidopiperidino)-propoxy]-2-methyl-4H-1-benzopyran-4-one

HRID 2296336Notes

Reaction equation

HRID 2296336 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[CH:7]=[C:8]([CH3:10])[O:9][C:4]=2[CH:3]=1.[Na].[C:15]([NH:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32]Cl)[CH2:26][CH2:25]1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(O)C>[C:15]([NH:23][CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][O:1][C:2]2[CH:13]=[CH:12][C:5]3[C:6](=[O:11])[CH:7]=[C:8]([CH3:10])[O:9][C:4]=3[CH:3]=2)[CH2:26][CH2:25]1)(=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 53553097-hydroxy-2-methyl-4H-1-benzopyran-4-oneHCID 5360545SodiumHCID 12799158N-[1-(3-Chloropropyl)piperidin-4-yl]benzamide

Product 1

HCID 131362197-[3-(4-Benzamidopiperidino)-propoxy]-2-methyl-4H-1-benzopyran-4-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

5.3 g. (0.03 mol) 7-hydroxy-2-methyl-4H-1-benzopyran-4-one are added to a solution of 0.69 g. (0.03 mol) sodium in 75 ml. propan-2-ol and the mixture heated under reflux for 10 minutes. 8.4 g. (0.03 mol) 3-(4-Benzamidopiperidino)-propyl chloride dissolved in 25 ml. propan-2-ol are added thereto, the mixture heated under reflux for 12 hours, evaporated and the residue taken up in dichloromethane and the solution washed with dilute aqueous sodium hydroxide solution. The organic phase is evaporated and the residue recrystallised from propan-2-ol. There are obtained 6.8 g. (54% of theory) 7-[3-(4-benzamidopiperidino)propoxy]-2-methyl-4H-1-benzopyran-2-one; m.p. 173°-175° C.

Workup

  1. temperatureunder reflux for 10 minutes
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 12 hours
  4. customevaporated
  5. washthe solution washed with dilute aqueous sodium hydroxide solution
  6. customThe organic phase is evaporated
  7. customthe residue recrystallised from propan-2-ol
  8. customThere are obtained 6.8 g

Sources & evidence

ORD record
ord-d949d67658e94c379e4281ea6f46e158
Source dataset
uspto-grants-1984_01
Patent number
US04428955

Reaction notes

Loading…