Formaldehyde → HCID 23299998, compound

HRID 1952745Notes

Reaction equation

HRID 1952745 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:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:21]=[C:20]([CH:29]2[CH2:31][CH2:30]2)[CH:19]=1>>[NH2:17][C:18]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:21]=[C:20]([CH:29]2[CH2:31][CH2:30]2)[C:19]=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 27580103-Cyclopropyl-1-phenyl-1H-pyrazol-5-amine

Product 1

HCID 23299998HCID 23299998, compound

Procedure

A mixture of 1-(2-methoxyphenyl)piperazine (2.4 g), 37-40% aqueous formaldehyde solution (0.9 ml) and industrial methylated spirit (30 ml) was stirred at ambient temperature under nitrogen for 18 hours, then a slurry of 5-amino-3-cyclopropyl-1-phenylpyrazole (2.5 g) in industrial methylated spirit (60 ml) was added in one portion. The stirred mixture was heated under reflux for 24 hours then the solvents were removed in vacuo. The residue was purified by reduced pressure column chromatography over silica using a 19:1 mixture of dichloromethane and industrial methylated spirit as eluant. Appropriate fractions were combined and the solvents removed in vacuo. The residue was triturated with acetone and the resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 5-amino-3-cyclopropyl-4-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]-1-phenylpyrazole as a white solid (1.4 g), m.p. 70-74° C.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 24 hours
  3. customthe solvents were removed in vacuo
  4. customThe residue was purified by reduced pressure column chromatography over silica using
  5. additiona 19:1 mixture of dichloromethane and industrial methylated spirit as eluant
  6. customthe solvents removed in vacuo
  7. customThe residue was triturated with acetone
  8. filtrationthe resulting solid was collected by filtration
  9. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-7046794e670244428fd5142911acae38
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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