Formaldehyde → HCID 23299981, compound

HRID 1952753Notes

Reaction equation

HRID 1952753 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.[CH3:19][CH:20]1[C:24](=[O:25])[NH:23][C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:21]1>>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:19][C:20]4([CH3:17])[C:24](=[O:25])[NH:23][C:22]([C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=5)=[N:21]4)[CH2:13][CH2:12]3)[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 65853EltoprazineHCID 23300038HCID 23300038, compound

Product 1

HCID 23299981HCID 23299981, compound

Procedure

A mixture of 1-(1,4-benzodioxan-5-yl)piperazine (4.96 g; prepared in a similar manner to that described in Example 2), 37-40% aqueous formaldehyde solution (1 ml) and industrial methylated spirit (40 ml) was stirred at ambient temperature under nitrogen for 30 minutes, then a suspension of 4-methyl-2-phenyl-2-imidazolin-5-one (3.82 g; prepared in a similar manner to that described in Example 37) in industrial methylated spirit (100 ml) was added in one portion. The mixture was stirred and heated under reflux for 18 hours, then the solvent was removed in vacuo. The residue was purified by flash chromatography over silica using a 1:1 mixture of ethyl acetate and ethanol as eluant. Appropriate fractions were combined and the solvents removed in vacuo to leave an oil. The oil was triturated with ethyl acetate, undissolved solid was removed by filtration, the filtrate was diluted with cyclohexane, and the resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 4-[4-(1,4-benzodioxan-5-yl)piperazin-1-ylmethyl]-4-methyl-2-phenyl-2-imidazolin-5-one 1.1 hydrate as an off-white solid (0.6 g), m.p. 80-85° C.

Workup

  1. customprepared in a similar manner to that
  2. customprepared in a similar manner to that
  3. additionwas added in one portion
  4. stirringThe mixture was stirred
  5. temperatureheated
  6. temperatureunder reflux for 18 hours
  7. customthe solvent was removed in vacuo
  8. customThe residue was purified by flash chromatography over silica using
  9. additiona 1:1 mixture of ethyl acetate and ethanol as eluant
  10. customthe solvents removed in vacuo
  11. customto leave an oil
  12. customThe oil was triturated with ethyl acetate, undissolved solid
  13. customwas removed by filtration
  14. additionthe filtrate was diluted with cyclohexane
  15. filtrationthe resulting solid was collected by filtration
  16. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-bce486b91dfd46dbb62e6819932e18d7
Source dataset
uspto-grants-2000_09
Patent number
US06114334

Reaction notes

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