Formaldehyde → 2-Phenyl-3-[3(N-methylpiperazino)propionyl]benzofuran

HRID 436496Notes

Reaction equation

HRID 436496 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.Cl.Cl.[CH3:23][N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.[C:30]1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>C(O)(C)C>[C:1]1([C:7]2[O:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11]=2[C:12](=[O:14])[CH2:13][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 27347151-Methylpiperazine dihydrochlorideHCID 130247261-(2-Phenylbenzofuran-3-yl)ethanone

Product 1

HCID 214527462-Phenyl-3-[3(N-methylpiperazino)propionyl]benzofuran

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 23.6 grams of 2-phenyl-3-acetylbenzofuran in 100 milliliters of isopropanol were added 4.2 grams of paraformaldehyde and 19.1 grams of N-methylpiperazine dihydrochloride and the mixture was heated under gentle reflux for a period of 12 hours. The dihydrochloride of the compound named in the heading of this example precipitated from the reaction mixture and was separated therefrom by suction filtration, washed with a small quantity of ethanol, and recrystallized from ethanol. The dihydrochloride had a melting point of 174°-177°C and 22.8 grams thereof was thus obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder gentle reflux for a period of 12 hours
  3. customprecipitated from the reaction mixture
  4. customwas separated
  5. filtrationby suction filtration
  6. washwashed with a small quantity of ethanol
  7. customrecrystallized from ethanol
  8. customthereof was thus obtained

Sources & evidence

ORD record
ord-6802c8bf4a2c4fd38383ba23faa78f69
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Reaction notes

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