1-Methylpiperazine → HCID 20347480, compound

HRID 1701280Notes

Reaction equation

HRID 1701280 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:13][C:14]1[CH:28]=[CH:27][CH:26]=[CH:25][C:15]=1[CH2:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([OH:24])=O.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>O1CCCC1>[NH2:13][C:14]1[CH:28]=[CH:27][CH:26]=[CH:25][C:15]=1[CH2:16][N:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:22]([N:33]1[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]1)=[O:24]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 12595981HCID 12595981, compound

Product 1

HCID 20347480HCID 20347480, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.40 g. of carbonyl diimidazole and 25 ml. of tetrahydrofuran is cooled and 4.32 g. of 1-o-aminobenzyl-2-pyrrolecarboxylic acid is added. The mixture is allowed to stand at 25°-30° C. for 30 minutes and 2.6 ml. of N-methylpiperazine is added. The mixture is allowed to stand 48 hours, then concentrated to about 1/2 volume and treated with ether. The mixture is filtered. The filtrate is evaporated to remove the solvent. The residue is treated with water and methylene chloride. The methylene chloride layer is separated and concentrated and further purified by partition chromatography giving 1-[1-(o-aminobenzyl)-2-pyrrolecarbonyl]-4-methylpiperazine as a viscous oil.

Workup

  1. additionA mixture of 3.40 g
  2. waitto stand 48 hours
  3. concentrationconcentrated to about 1/2 volume
  4. additiontreated with ether
  5. filtrationThe mixture is filtered
  6. customThe filtrate is evaporated
  7. customto remove the solvent
  8. additionThe residue is treated with water and methylene chloride
  9. customThe methylene chloride layer is separated
  10. concentrationconcentrated
  11. customfurther purified
  12. customby partition chromatography

Sources & evidence

ORD record
ord-bcc774138bcd4c11bb3645e733ad8e47
Source dataset
uspto-grants-1980_03
Patent number
US04192803

Reaction notes

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