Formaldehyde → 2-Phenyl-3-(3-morpholinopropionyl)benzofuran

HRID 436494

Reaction equation

HRID 436494 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.[CH2:19]=O.Cl.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>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][CH2:19][N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 197884Morpholine, hydrochloride (1:1)HCID 130247261-(2-Phenylbenzofuran-3-yl)ethanone

Product 1

HCID 214527432-Phenyl-3-(3-morpholinopropionyl)benzofuran

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 23.6 grams of 2-phenyl-3- acetylbenzofuran, 70 milliliters of isopropanol, 4.2 grams of paraformaldehyde, and 17.3 grams of morpholine hydrochloride were heated under reflux at the boiling point for 12 hours, after which the solvent was evaporated therefrom under vacuum and the residue was triturated with dilute hydrochloric acid and the hydrochloride of the compound named in the heading of this example, which separated in the form of crystals therefrom, was separated from the mixture by suction filtration and dried. In this manner, 23.8 grams of the specified hydrochloride, which had a melting point of 177°-179°C, was obtained.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux at the boiling point for 12 hours
  3. customafter which the solvent was evaporated
  4. customunder vacuum and the residue was triturated with dilute hydrochloric acid
  5. customseparated in the form of crystals
  6. customwas separated from the mixture by suction filtration
  7. customdried
  8. customwas obtained

Sources & evidence

ORD record
ord-97fbee31cadf452da5ea122f3924efeb
Source dataset
uspto-grants-1977_02
Patent number
US04009184

Linked notes

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