Formaldehyde → HCID 9823511, compound

HRID 1952743Notes

Reaction equation

HRID 1952743 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1.[CH2:17]=O.[NH2:19][C:20]1[N:21]([CH3:32])[N:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:25])[CH:24]=1>>[NH2:19][C:20]1[N:21]([CH3:32])[N:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:23](=[O:25])[C:24]=1[CH2:17][N:14]1[CH2:15][CH2:16][N:11]([C:10]2[C:5]3[O:4][CH2:3][CH2:2][O:1][C:6]=3[CH:7]=[CH:8][CH:9]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 65853EltoprazineHCID 11008703HCID 11008703, compound

Product 1

HCID 9823511HCID 9823511, compound

Procedure

A mixture of 1-(1,4-benzodioxan-5-yl)piperazine (2.45 g), 37-40% aqueous formaldehyde solution (0.8 ml) and industrial methylated spirit (30 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 (1.95 g) in industrial methylated spirit (55 ml) was added in one portion. The stirred mixture was heated under reflux for 5 hours, then allowed to stand at ambient temperature for 18 hours. The resulting solid was collected by filtration, and the filtrate was concentrated in vacuo to 40 ml then cooled in ice to give a second crop of white solid which was collected by filtration. The combined solids were suspended in industrial methylated spirit (80 ml), and the mixture was heated to reflux temperature. Undissolved solid was removed by filtration of the hot mixture, then the filtrate was concentrated to 40 ml, cooled in ice, and the resulting solid was collected by filtration. The two crops of solid were combined and dried in vacuo at 65° C. to give 3-amino-4-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-2-methyl-1-phenyl-3-pyrazolin-5-one 0.75 hydrate as a white solid (2.45 g), m.p. 222-224° C.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 5 hours
  3. waitto stand at ambient temperature for 18 hours
  4. filtrationThe resulting solid was collected by filtration
  5. concentrationthe filtrate was concentrated in vacuo to 40 ml
  6. temperaturethen cooled in ice
  7. customto give a second crop of white solid which
  8. filtrationwas collected by filtration
  9. temperaturethe mixture was heated
  10. temperatureto reflux temperature
  11. customwas removed by filtration of the hot mixture
  12. concentrationthe filtrate was concentrated to 40 ml
  13. temperaturecooled in ice
  14. filtrationthe resulting solid was collected by filtration
  15. customdried in vacuo at 65° C.

Sources & evidence

ORD record
ord-e62184ce971443eba97bb42f9a754244
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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