Formaldehyde → HCID 9823511, compound

HRID 1952744Notes

Reaction equation

HRID 1952744 reaction equation
[CH2:1]=O.[O:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[C:7]=2[O:6][CH2:5][CH2:4]1.[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>C(O)C>[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[CH2:1][N:16]1[CH2:17][CH2:18][N:13]([C:12]2[C:7]3[O:6][CH2:5][CH2:4][O:3][C:8]=3[CH:9]=[CH:10][CH:11]=2)[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 65853EltoprazineHCID 11008703HCID 11008703, compound

Product 1

HCID 9823511HCID 9823511, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

37-40% Aqueous formaldehyde solution (12.4 ml) was added to a solution of 1-(1,4-benzodioxan-5-yl)piperazine (33.1 g; prepared in a similar manner to that described in Example 2 above) in absolute ethanol (250 ml) and the mixture stirred at ambient temperature for 3 hours. The mixture was diluted with absolute ethanol (500 ml) and the resulting solution stirred at ambient temperature for 19 hours. A solution of 3-amino-2-methyl-1-phenyl-3-pyrazolin-5-one (31.7 g) in absolute ethanol (1000 ml) was added and the solution stirred at ambient temperature for 23 hours. The resulting solid was collected by filtration, dried in vacuo at ambient temperature, and suspended in ethyl acetate (1200 ml). The mixture was stirred and heated under reflux for 66 hours, and the resulting solid was collected by hot filtration, dried in vacuo at ambient temperature, ground with a mortar and pestle then again stirred and heated under reflux with ethyl acetate (1700 ml) for 46 hours. The product was collected by hot filtration, then dried in vacuo at ambient temperature to give 3-amino-4-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-2-methyl-1-phenyl-3-pyrazolin-5-one as a white solid (50.4 g), m.p. 223-224° C.

Workup

  1. customprepared in a similar manner to that
  2. stirringthe resulting solution stirred at ambient temperature for 19 hours
  3. stirringthe solution stirred at ambient temperature for 23 hours
  4. filtrationThe resulting solid was collected by filtration
  5. customdried in vacuo at ambient temperature
  6. stirringThe mixture was stirred
  7. temperatureheated
  8. temperatureunder reflux for 66 hours
  9. filtrationthe resulting solid was collected by hot filtration
  10. customdried in vacuo at ambient temperature
  11. stirringground with a mortar and pestle then again stirred
  12. temperatureheated
  13. temperatureunder reflux with ethyl acetate (1700 ml) for 46 hours
  14. filtrationThe product was collected by hot filtration
  15. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-d5e89f94e0b9421894979dd8be988501
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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