Piperidine → HCID 46916365, compound

HRID 2045919Notes

Reaction equation

HRID 2045919 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:21]=[N:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[NH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(OCC)(=O)C>CC#N>[N:28]1([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([C:12]3[CH:21]=[N:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[N:13]=3)[CH:7]=2)=[O:4])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 46916365HCID 46916365, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (100 mg, 0.336 mmol) and K2CO3 (56 mg, 0.403 mmol) in MeCN (5 mL), piperidine (35 μL, 0.353 mmol) was added and the reaction mixture was stirred at reflux for 18 hrs. The solvent was evaporated in vacuo and the residue was purified by flash chromatography (Flash Master, Isolute 5 g silica, gradient 0-5 min, 100% hexane and then 0-100% ethyl acetate over 40 min) to afford 2-(piperidin-1-yl)-N-[3-(quinoxalin-2-yl)phenyl]acetamide (50 mg, 42% yield). LCMS calculated for C21H22N4O (M+H): 347.18. found 347. 1H-NMR (DMSO-d6, 400 Mhz) δH: 9.88 (1H, br. s), 9.48 (1H, s), 8.54 (1H, m), 8.12-8.10 (2H, m), 7.98 (1H, d, J=7 Hz), 7.91-7.81 (3H, m), 7.52 (1H, m), 3.12 (2H, s), 2.55-2.53 (4H, m), 1.61-1.55 (4H, m), 1.42-1.36 (2H, m).

Workup

  1. temperatureat reflux for 18 hrs
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by flash chromatography (Flash Master, Isolute 5 g silica, gradient 0-5 min, 100% hexane

Sources & evidence

ORD record
ord-b2add2e4212b40efaaf022faca4cf1d8
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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