1-Piperonylpiperazine → HCID 178419743, compound

HRID 466993Notes

Reaction equation

HRID 466993 reaction equation
[Br:1][CH2:2][CH:3]1[CH2:16][N:6]2[C:7](=[O:15])[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4]1.[CH2:17]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:18]1[CH:26]=[CH:25][C:24]2[O:23][CH2:22][O:21][C:20]=2[CH:19]=1>C(#N)C>[BrH:1].[CH2:17]([N:27]1[CH2:32][CH2:31][N:30]([CH2:2][CH:3]2[CH2:16][N:6]3[C:7](=[O:15])[NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=4[C:5]3=[N:4]2)[CH2:29][CH2:28]1)[C:18]1[CH:26]=[CH:25][C:24]2[O:23][CH2:22][O:21][C:20]=2[CH:19]=1.[CH3:2][CH:3]1[CH2:16][N:6]2[C:7](=[O:15])[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:5]2=[N:4]1

Participants

5

Reactant 2

HCID 944261-PiperonylpiperazineHCID 178517109HCID 178517109, compound

Product 2

HCID 178419743HCID 178419743, compoundYield 67%HCID 178429828HCID 178429828, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromomethyl-2,3-dihydroimidazo[1,2-c]-quinazolin-5(6H)-one (0.5 g, 1.78 mmol), 1-piperonylpiperazine (0.78 g, 3.56 mmol) in acetonitrile (25 mL) was refluxed for 17 hours. The solvent was then removed in vacuo to the oily residue. The residue was purified by column chromatography [silica gel: 25 g, column diameter: 2.5 cm, solvent system: chloroform/ethylacetate (9/1)] to furnish 2-[4-piperonyl-1-piperazinyl]methyl-2,3-dihydroimidazo[1,2-c]-quinazolin-5(6H)-one hydrobromide (620 mg, 67%) and 2-methyl-2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-one (90 mg, 22%). 2-[4-piperonyl-1-piperazinyl]methyl-2,3-dihydroimidazo[1,2-c]-quinazolin-5(6H)-one hydrobromide: mp 236°-238° C. Anal. Calcd for C23H23N5O3 /H2O/HBr: C, 53.29; H, 5.44; N, 13.50. Found: C, 53.45; H, 5.46 ; N, 13.54.

Workup

  1. temperaturewas refluxed for 17 hours
  2. customThe solvent was then removed in vacuo to the oily residue
  3. customThe residue was purified by column chromatography [silica gel: 25 g, column diameter: 2.5 cm, solvent system: chloroform/ethylacetate (9/1)]

Sources & evidence

ORD record
ord-4dfeb3a9e7a04fab833fe6c2b1ff162b
Source dataset
uspto-grants-1992_10
Patent number
US05158953

Reaction notes

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