3-Chloropropyl(diethyl)amine → 3-p-Toluoyl-2-[4-(3-diethylaminopropoxy)phenyl]benzofuran

HRID 1414604Notes

Reaction equation

HRID 1414604 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=3[C:13]=2[C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32]Cl)[CH3:28]>C1(C)C=CC=CC=1.CO>[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]3[CH:26]=[CH:25][CH:24]=[CH:23][C:12]=3[C:13]=2[C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:7][CH:8]=1)[CH3:28]

Participants

6

Reactant 3

HCID 669183-Chloropropyl(diethyl)amineHCID 5360545SodiumHCID 214879512-p-Hydroxyphenyl-3-p-methylbenzoylbenzofuran

Product 1

HCID 103677653-p-Toluoyl-2-[4-(3-diethylaminopropoxy)phenyl]benzofuran

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent2×

Procedure

To a solution of 0.177 g. (7.7 g.-atom) of sodium dissolved in 25 ml. of dry methanol was added a solution of 2.4 g. (7.3 mmol.) of 2-p-hydroxyphenyl-3-p-methylbenzoylbenzofuran in 75 ml. of toluene and 10 ml. of methanol. The mixture was refluxed for 15 minutes, then the methanol was removed by distillation. A solution of 1.15 g. (7.7 mmol.) of 3-diethylaminopropyl chloride in 25 ml. of toluene was then added and the resulting mixture was refluxed for 6 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated to give the title compound.

Workup

  1. temperatureThe mixture was refluxed for 15 minutes
  2. customthe methanol was removed by distillation
  3. temperaturethe resulting mixture was refluxed for 6 hours
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d08a998f14d34d68b027e1aa84a112db
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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