Pyrrolidine → 6-[3-(pyrrolidin-1-yl)propoxy]-3,4-dihydroquinolin-2(1H)-one

HRID 1913892Notes

Reaction equation

HRID 1913892 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>CC(O)C.O>[N:17]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]3)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 110428286-(3-Chloropropoxy)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 130542126-[3-(pyrrolidin-1-yl)propoxy]-3,4-dihydroquinolin-2(1H)-oneYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 6-(3-chloropropoxy)-3,4-dihydroquinolin-2(1H)-one prepared in Example 10-(1) (10 g) and pyrrolidine (15 g) in 2-propanol (15 mL) was stirred at 90° C. for 2 days. The reaction mixture was cooled to room temperature, diluted with water and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform→chloroform/methanol=4/1), and the resulting solid was subjected to recrystallization from ethyl acetate to give the titled compound (7.5 g, 65%) as a colorless solid.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluting solvent: chloroform→chloroform/methanol=4/1)
  6. customthe resulting solid was subjected to recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d388dbaa2ed446c89afbda8d3a556176
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

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