Dimethylamine → HCID 131730512, compound

HRID 1966558Notes

Reaction equation

HRID 1966558 reaction equation
C([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11](Cl)[CH:10]=1)C1C=CC=CC=1.[CH3:20][NH:21][CH3:22]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O>[CH2:9]([C:10]1[C:11]([N:21]([CH3:22])[CH3:20])=[N:12][C:13]2[C:18]([C:9]=1[NH2:8])=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:18]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 59474772HCID 59474772, compound

Product 1

HCID 131730512HCID 131730512, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent

Procedure

Benzyl-(2-chloroquinolin-4-yl)-amine (100 mg, 0.372 mmole), copper(II)sulphate pentahydrate (92.9 mg, 0.372 mmole) and dimethylamine (1M in MeOH, 3 mL) were stirred at 150° C. in a microwave oven for 5 hrs. The reaction mixture was dissolved with water and extracted with ethyl acetate. The residue obtained from the organic phases was purified using silica gel chromatography, eluting with dichloromethane:methanol 90:10. Precipitation in isopropyl ether gave a yellowish solid (70.0 mg, 68%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe residue obtained from the organic phases
  3. customwas purified
  4. washeluting with dichloromethane:methanol 90:10
  5. customPrecipitation in isopropyl ether

Sources & evidence

ORD record
ord-1af71e3587c744b28e7a819b7686339d
Source dataset
uspto-grants-2013_04
Patent number
US08420670B2

Reaction notes

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