1-(2-Methoxyphenyl)piperazine → HCID 21481012, compound

HRID 1490331Notes

Reaction equation

HRID 1490331 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:13][O:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH2:23][CH2:24][C:25]([O:27]CC)=O)=[C:17]([N:30]2[CH:34]=[CH:33][CH:32]=[CH:31]2)[CH:16]=1.[CH3:35][O:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>O1CCCC1>[CH3:13][O:14][C:15]1[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH2:23][CH2:24][C:25]([N:46]2[CH2:45][CH2:44][N:43]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[O:36][CH3:35])[CH2:48][CH2:47]2)=[O:27])=[C:17]([N:30]2[CH:31]=[CH:32][CH:33]=[CH:34]2)[CH:16]=1

Participants

5

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 682631,1'-CarbonyldiimidazoleHCID 21480996HCID 21480996, compound

Product 1

HCID 21481012HCID 21481012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 20 ml of tetrahydrofuran was dissolved 1.20 g of N,N-carbonyldiimidazole, and a solution of 2.0 g of ethyl 3-(4,5-dimethoxy-2-(1-pyrrolyl)phenyl)propionate in 40 ml of tetrahydrofuran was added to the solution at room temperature while stirring. The stirring was continued at that temperature for additional 1 hour, 2.98 g of 1-(2-methoxyphenyl)piperazine was added thereto, followed by stirring at 40° to 60° C. for 6 hours. The solvent was removed under reduced pressure, and the residue was purified by silica gel colunun chromatography (chloroform-methanol) to yield 1.9 g of a colorless oily substance. Recrystallization from ethanol gave the title compound as a colorless crystal.

Workup

  1. stirringby stirring at 40° to 60° C. for 6 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by silica gel colunun chromatography (chloroform-methanol)
  4. customto yield 1.9 g of a colorless oily substance
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-9970c2bf194a4879bc801530ef8b3998
Source dataset
uspto-grants-1997_10
Patent number
US05681954

Reaction notes

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