Piperazine → 6-Methoxy-2-piperazin-1-yl-quinoline

HRID 860015Notes

Reaction equation

HRID 860015 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[N:3]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 4837PiperazineHCID 836472-Chloro-6-methoxyquinoline

Product 1

HCID 216804206-Methoxy-2-piperazin-1-yl-quinolineYield 50.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-chloro-6-methoxy-quinoline of Step C, (2.5 g, 12.91 mmol) in N,N-dimethylformamide (50 mL) is added piperazine (12 g) and the mixture is heated at 110° C. under nitrogen for 6 hours. The solution is diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extracts are dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is flash chromatographed on silica gel Merck-60 using a gradient of methanol (4–10%) in dichloromethane containing 0.2% ammonium hydroxide to provide the title compound (1.6 g) as an off-white solid, m.p. 95–97° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried over anhydrous magnesium sulfate
  3. customevaporated to dryness
  4. customchromatographed on silica gel Merck-60

Sources & evidence

ORD record
ord-d8c3e0df2fb34acb97f4ba74f0feb8ac
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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