Piperazine → N,N-diethyl-4-(1-piperazinyl(8-quinolinyl)methyl)benzamide

HRID 1837545Notes

Reaction equation

HRID 1837545 reaction equation
Cl[CH:2]([C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)[C:3]1[CH:15]=[CH:14][C:6]([C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CC#N>[CH2:10]([N:9]([CH2:12][CH3:13])[C:7](=[O:8])[C:6]1[CH:14]=[CH:15][C:3]([CH:2]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[CH:4][CH:5]=1)[CH3:11]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 226778764-[chloro(8-quinolinyl)methyl]-N,N-diethylbenzamide

Product 1

HCID 9801260N,N-diethyl-4-(1-piperazinyl(8-quinolinyl)methyl)benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The crude product compound III (˜6.6 mmol) and piperazine (2.3 g, 26 mmol) was dissolved in dry MeCN (50 mL) and heated at reflux 12 h. The solvent was removed in vacuo, the residue dissolved in CH2Cl2 and washed with water and the organic phase dried (K2CO3) and evaporated in vacuo. After chromatography on silica (0-20% MeOH in CH2Cl2, 1% NH4OH), a total of 1.8 g (68%, 2 steps) compound 1 was obtained. Further purification could be achieved by reverse phase chromatograpy (LiChroprep RP-18, 10-50% MeCN in water, 0.1% TFA) to give 1.2 g colorless product. The dihydrochloride salt was made by treatment with 2 eq. HCl in ether.

Workup

  1. temperatureheated
  2. temperatureat reflux 12 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in CH2Cl2
  5. washwashed with water
  6. dry with materialthe organic phase dried (K2CO3)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a6f80fafb89e4be08d1c7a50e2d06e0a
Source dataset
uspto-grants-2004_08
Patent number
US06784181B2

Reaction notes

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