Piperazine → 4-(6-Fluoroquinolin-2-yl)piperazine-1-carbaldehyde

HRID 860024Notes

Reaction equation

HRID 860024 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:12])[CH:8]=2)[N:3]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[C:19](=O)(O)[O-:20].[Na+]>CN(C)C=O>[F:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:13]1[CH2:18][CH2:17][N:16]([CH:19]=[O:20])[CH2:15][CH2:14]1)[CH:11]=[CH:10]2

Participants

5

Reactant 3

HCID 4837PiperazineHCID 516892Sodium BicarbonateHCID 150594332-Chloro-6-fluoroquinoline

Product 1

HCID 587653254-(6-Fluoroquinolin-2-yl)piperazine-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-6-fluoroquinoline from Step D (0.8 g, 4.4 mmol) and piperazine (3.79 g, 44 mmol) in N,N-dimethylformamide (20 mL) is heated at 110° C. for 2 hours. The reaction is then basified with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated to give a tan oil. The oil is flash chromatographed on silica gel Merck-60 with a gradient of methanolic ammonia (5–10%) in ethyl acetate to provide the title compound (0.330 g) as an off-white solid, m.p. 110–111° C.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts are dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a tan oil
  6. customchromatographed on silica gel Merck-60 with a gradient of methanolic ammonia (5–10%) in ethyl acetate

Sources & evidence

ORD record
ord-b54080606cc74598ab86691ec2f68e88
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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