Hydrochloric Acid → HCID 59397851, compound

HRID 39679

Reaction equation

HRID 39679 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]1=[O:11].[H-].[Na+].CS(O[CH2:19][CH2:20][CH2:21][C:22]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)(=O)=O.Cl>O.C(OCC)(=O)C.CN(C)C=O>[O:11]=[C:2]1[CH:3]=[N:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]1[CH2:19][CH2:20][CH2:21][C:22]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:24][CH2:23]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 145262(1H)-QuinoxalinoneHCID 24758Sodium hydrideHCID 578155261-Tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate

Product 1

HCID 59397851HCID 59397851, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To 5 mL of an N,N-dimethylformamide suspension containing 0.25 g of quinoxalin-2(1H)-one, 0.10 g of 60% sodium hydride was added at room temperature, and the mixture was stirred at 50° C. for 30 minutes. Thereto was dividedly added 0.68 g of 1-tert-butyl 4-ethyl 4-(3-((methanesulfonyl)oxy)propyl)piperidine-1,4-dicarboxylate at the same temperature, and the mixture was stirred at 80 to 90° C. for 2 hours. The reaction mixture was cooled to room temperature, ethyl acetate and water were added thereto, and the resultant solution was adjusted to pH 2.0 with 6 mol/L hydrochloric acid. 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 sequentially with water and 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 0.18 g of a yellow brown oily substance, 1-tert-butyl 4-ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)piperidine-1,4-dicarboxylate.

Workup

  1. additionwas added at room temperature
  2. stirringthe mixture was stirred at 80 to 90° C. for 2 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washthe resultant solution was washed sequentially with water
  7. dry with materialan aqueous saturated sodium chloride solution and dried 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-904ce44749514eb596dba1bec9ba4ac8
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Linked notes

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