3-Phenylpyrrolidine → 6-Chloro-2-methyl-4-(3-phenylpyrrolidin-1-yl)quinoline

HRID 408657Notes

Reaction equation

HRID 408657 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[C:14]1([CH:20]2[CH2:24][CH2:23][NH:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCCO)C.O>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[N:22]1[CH2:23][CH2:24][CH:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:21]1

Participants

5

Reactant 2

HCID 31467433-PhenylpyrrolidineHCID 123225774,6-Dichloro-2-methylquinoline

Product 1

HCID 251156406-Chloro-2-methyl-4-(3-phenylpyrrolidin-1-yl)quinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

4,6-Dichloro-2-methylquinoline (0.1 g) and 3-phenylpyrrolidine (0.15 g) in 2-ethoxy-ethanol (1.5 mL) was heated in a microwave at 240° C. for 10 minutes. The mixture was diluted with water and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica, eluting with a mixture of methanol and dichloromethane. Evaporation of the desired fractions gave the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica
  7. washeluting with a mixture of methanol and dichloromethane
  8. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-04d216d25528435193ed1b07fcb00c01
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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