Dimethylformamide → HCID 59398042, compound

HRID 39791Notes

Reaction equation

HRID 39791 reaction equation
CN(C)C=O.[O:6]=[C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]1[CH2:17][CH2:18][CH2:19][C:20]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Br[CH2:32][CH2:33][S:34][C:35]1[S:36][CH:37]=[CH:38][CH:39]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[O:6]=[C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]1[CH2:17][CH2:18][CH2:19][C:20]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:25][CH2:24][N:23]([CH2:32][CH2:33][S:34][C:35]2[S:36][CH:37]=[CH:38][CH:39]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 122011192-(2-Bromoethylthio)-thiophene2×HCID 59398082ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)piperidine-4-carboxylate

Product 1

HCID 59398042HCID 59398042, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
52.5 °C

Procedure

To 2 mL of an N,N-dimethylformamide solution containing 95 mg of ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)piperidine-4-carboxylate, 69 mg of 2-(2-bromoethylthio)thiophene and 84 mg of potassium carbonate were added at room temperature, and stirred at 50-55° C. for 1 hour. Additional 35 mg of 2-(2-bromoethylthio)thiophene was added and stirred at 50-55° C. for 1 hour, then stirred at 60° C. for 1 hour. The mixture was cooled to the room temperature, ethyl acetate and water were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, 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; chloroform:methanol=20:1] to give 98 mg of ethyl 4-(3-(2-oxoquinoxalin-1(2H)-yl)propyl)-1-(2-(2-thienylthio)ethyl)piperidine-4-carboxylate as a light brown oil.

Workup

  1. additionwere added at room temperature
  2. stirringstirred at 50-55° C. for 1 hour
  3. stirringstirred at 60° C. for 1 hour
  4. additionwere added
  5. customthe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washwashed sequentially with water and aqueous saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-a42f80312fff4f80b125af1b16a10ea6
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…