3-Phenylpyrrolidine → Benzyl-[2-methyl-4-(3-phenylpyrrolidin-1-yl)quinolin-6-yl]amine

HRID 408664Notes

Reaction equation

HRID 408664 reaction equation
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH3:19])[CH:13]=[C:12]2Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]1([CH:27]2[CH2:31][CH2:30][NH:29][CH2:28]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCCO)C.O>[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[C:14]([CH3:19])[CH:13]=[C:12]2[N:29]1[CH2:30][CH2:31][CH:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:28]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31467433-PhenylpyrrolidineHCID 68729251Benzyl-(4-chloro-2-methylquinolin-6-yl)amine

Product 1

HCID 25116794Benzyl-[2-methyl-4-(3-phenylpyrrolidin-1-yl)quinolin-6-yl]amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

Benzyl-(4-chloro-2-methylquinolin-6-yl)amine (0.041 g; see Preparation 4 above) and 3-phenylpyrrolidine in 2-ethoxyethanol (1 mL) were heated in a microwave to 240° C. for 10 minutes. The reaction 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 dichloromethane, and methanol. The desired fractions were concentrated and the sample evaporated to dryness. Trituration from ether gave the title compound.

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 dichloromethane, and methanol
  8. concentrationThe desired fractions were concentrated
  9. customthe sample evaporated to dryness

Sources & evidence

ORD record
ord-4c1e8d716bf74b218b2492aa54c87aa1
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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