Formaldehyde → HCID 23300029, compound

HRID 1952740Notes

Reaction equation

HRID 1952740 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.[NH2:17][C:18]1[N:19]([CH3:30])[N:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21](=[O:23])[CH:22]=1>>[OH2:2].[NH2:17][C:18]1[N:19]([CH3:30])[N:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:21](=[O:23])[C:22]=1[CH2:15][N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 13461-(2-Methoxyphenyl)piperazineHCID 11008703HCID 11008703, compound

Product 1

HCID 23300029HCID 23300029, compound

Procedure

A mixture of 1-(2-methoxyphenyl)piperazine (2.16 g), 37-40% aqueous formaldehyde solution (0.8 ml) and industrial methylated spirit (27 ml) was stirred at ambient temperature under nitrogen for 18 hours, then a slurry of 3-amino-2-methyl-1-phenyl-3-pyrazolin-5-one (2.14 g) in industrial methylated spirit (54 ml) was added in one portion. The stirred mixture was heated under reflux for 24 hours, allowed to cool to ambient temperature, and the resulting solid was collected by filtration, washed with industrial methylated spirit, and dried in vacuo at 50° C. to give 3-amino-4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-2-methyl-1-phenyl-3-pyrazolin-5-one monohydrate as an off-white solid (3.2 g), m.p. 133-136° C.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureto cool to ambient temperature
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with industrial methylated spirit
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-52ca630b2d484cf691b0c2600a183f7e
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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