Dimethylformamide → 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate

HRID 2193041Notes

Reaction equation

HRID 2193041 reaction equation
CN(C)C=O.[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([CH3:19])=[CH:13][C:14](=[O:18])[NH:15]2)=[CH:10][CH:9]=1.[H-].[Na+].CS(O[CH2:27][CH2:28][CH2:29][C:30]1([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1)(=O)=O>C(OCC)(=O)C.O>[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([CH3:19])=[CH:13][C:14](=[O:18])[N:15]2[CH2:27][CH2:28][CH2:29][C:30]2([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:32][CH2:31]2)=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 7615487-Methoxy-4-methylquinolin-2-olHCID 578155261-Tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate

Product 1

HCID 593981031-tert-butyl 4-ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 5 mL of an N,N-dimethylformamide suspension containing 0.50 g of 7-methoxy-4-methylquinolin-2(1H)-one, 0.11 g of 60% sodium hydride was added, and the mixture was stirred at 60° C. for 20 minutes. Thereto was added 1.09 g of 1-tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate, the temperature of the reaction mixture was increased to 70° C., and the reaction mixture was stirred for 4 hours. Thereto was added 0.11 g of 60% sodium hydride, and the resultant solution was stirred for 4 hours. Water and ethyl acetate were then added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:1] to obtain 0.45 g of a yellow oily substance, 1-tert-butyl 4-ethyl 4-(3-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate.

Workup

  1. additionwas added
  2. temperaturethe temperature of the reaction mixture was increased to 70° C.
  3. stirringthe reaction mixture was stirred for 4 hours
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:1]

Sources & evidence

ORD record
ord-1159b653eccd4e198ec3cf197c71fab9
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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