2-Methoxy-2,4,6-cycloheptatrien-1-one → 2-(4-Piperonyl-1-piperazinyl)-2,4,6-cycloheptatriene-1-one

HRID 609584Notes

Reaction equation

HRID 609584 reaction equation
CO[C:3]1[C:9](=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:11]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)[C:12]1[CH:20]=[CH:19][C:18]2[O:17][CH2:16][O:15][C:14]=2[CH:13]=1>CO>[CH2:11]([N:21]1[CH2:26][CH2:25][N:24]([C:3]2[C:9](=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:23][CH2:22]1)[C:12]1[CH:20]=[CH:19][C:18]2[O:17][CH2:16][O:15][C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 165462-Methoxy-2,4,6-cycloheptatrien-1-oneHCID 944261-Piperonylpiperazine

Product 1

HCID 98402272-(4-Piperonyl-1-piperazinyl)-2,4,6-cycloheptatriene-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-methoxytropone (1.36 g, 10.0 mmol) (Pietra, F. Chem Review, 1973, 73:293) and 1-piperonylpiperazine (6.61 g, 30.0 mmol) in methanol (50.0 mL) was refluxed for 16 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to column chromatography using ethyl acetate as the eluent. The title compound was obtained as a yellow oil (1.24 g, 38%). MS (FAB) 325 (M+ +1).

Workup

  1. temperaturewas refluxed for 16 h
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cff103170fa347b5a3c1344cde5b35a5
Source dataset
uspto-grants-1999_12
Patent number
US05998414

Reaction notes

Loading…