Formaldehyde → HCID 23300006, compound

HRID 1952750Notes

Reaction equation

HRID 1952750 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:25]=[N:26][CH:27]=[CH:28][CH:29]=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]=[N: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 23299969HCID 23299969, compound

Product 1

HCID 23300006HCID 23300006, compound

Procedure

A mixture of 1-(2-methoxyphenyl)piperazine (1.65 g) and 37-40% aqueous formaldehyde solution (0.39 ml) was stirred at ambient temperature under nitrogen for 10 minutes, then a suspension of 4-methyl-2-(3-pyridyl)-2-imidazolin-5-one (1.5 g) in industrial methylated spirit (75 ml) was added in one portion. The mixture was stirred and heated under reflux for 52 hours, then the solvent was removed in vacuo. The residue was triturated with a 49:49:2 mixture of ether, ethyl acetate and propan-2-ol, and the resulting solid was collected by filtration, washed with ethyl acetate, and dried in vacuo at ambient temperature to give 4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-4-methyl-2-(3-pyridyl)-2-imidazolin-5-one as an off-white solid (1.55 g), m.p. 159-162° C.

Workup

  1. additionwas added in one portion
  2. stirringThe mixture was stirred
  3. temperatureheated
  4. temperatureunder reflux for 52 hours
  5. customthe solvent was removed in vacuo
  6. customThe residue was triturated with a 49:49:2 mixture of ether, ethyl acetate and propan-2-ol
  7. filtrationthe resulting solid was collected by filtration
  8. washwashed with ethyl acetate
  9. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-c7f1285b04434151b42841b4608e89b3
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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