1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-[(2-Methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazine

HRID 377868Notes

Reaction equation

HRID 377868 reaction equation
[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14](=[O:22])OC2C=CC=CC=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1.C1CCN2C(=NCCC2)CC1>O1CCCC1>[CH3:1][O:2][C:3]1[C:12]([NH:13][C:14]([N:36]2[CH2:35][CH2:34][N:33]([C:27]3[CH:26]=[C:25]([O:24][CH3:23])[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=3)[CH2:38][CH2:37]2)=[O:22])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27362051-(3,5-Dimethoxyphenyl)piperazineHCID 19356985Phenyl N-(2-methoxyquinolin-3-yl)carbamate

Product 1

HCID 193569681-[(2-Methoxyquinolin-3-yl)aminocarbonyl]-4-(3,5-dimethoxyphenyl)piperazineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyl N-(2-methoxyquinolin-3-yl)carbamate(148 mg, 0.5 mmol) and 1-(3,5-dimethoxyphenyl)piperazine(112 mg, 0.5 mmol) were dissolved in anhydrous tetrahydrofuran and DBU(117 mg, 0.75 mmol) was added. The solution was stirred at room temperature for 2 hours. The mixture was concentrated under the reduced pressure to remove tetrahydrofuran and purified by column chromatography(hexane:ether=5:1) to obtain the titled compound.

Workup

  1. concentrationThe mixture was concentrated under the reduced pressure
  2. customto remove tetrahydrofuran
  3. custompurified by column chromatography(hexane:ether=5:1)

Sources & evidence

ORD record
ord-7e9413f597074816812d10d8ad9a712d
Source dataset
uspto-grants-2000_02
Patent number
US06028195

Reaction notes

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