Formaldehyde → HCID 23299977, compound

HRID 1952752Notes

Reaction equation

HRID 1952752 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH2:15]=O.[CH3:17][CH:18]1[C:22](=[O:23])[NH:21][C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:19]1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:17][C:18]2([CH3:15])[C:22](=[O:23])[NH:21][C:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[N:19]2)[CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 13461-(2-Methoxyphenyl)piperazineHCID 23300038HCID 23300038, compound

Product 1

HCID 23299977HCID 23299977, compound

Procedure

A mixture of 1-(2-methoxyphenyl)piperazine (2.4 g) and 37-40% aqueous formaldehyde solution was stirred at ambient temperature under nitrogen for 10 minutes, then a suspension of 4-methyl-2-phenyl-2-imidazolin-5-one (2.58 g) in industrial methylated spirit (100 ml) was added in one portion. The stirred mixture was heated under reflux for 48 hours, then the solvent was removed in vacuo. The residue was triturated with a 2:1 mixture of cyclohexane and ether, undissolved solid was removed by filtration, then the filtrate was allowed to concentrate at ambient temperature. The resulting solid was collected by filtration. Further concentration of the filtrate yielded a second crop of solid. The two crops of solid were combined and dried in vacuo at ambient temperature to give 4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-4-methyl-2-phenyl-2-imidazolin-5-one 1.1 hydrate as a colourless solid (0.2 g), m.p. 86-89° C.

Workup

  1. additionwas added in one portion
  2. temperatureThe stirred mixture was heated
  3. temperatureunder reflux for 48 hours
  4. customthe solvent was removed in vacuo
  5. customThe residue was triturated with a 2:1 mixture of cyclohexane and ether, undissolved solid
  6. customwas removed by filtration
  7. concentrationto concentrate at ambient temperature
  8. filtrationThe resulting solid was collected by filtration
  9. customFurther concentration of the filtrate yielded a second crop of solid
  10. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-70ddd486e3984fcca70bfc9efd86815e
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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