Potassium Carbonate → HCID 46917072, compound

HRID 2045914Notes

Reaction equation

HRID 2045914 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].Cl.Cl.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.C(OCC)(=O)C>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([N:31]2[CH2:36][CH2:35][N:34]([CH2:2][C:3]([NH:5][C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([C:12]4[CH:21]=[N:20][C:19]5[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:13]=4)[CH:7]=3)=[O:4])[CH2:33][CH2:32]2)=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamideHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)

Product 1

HCID 46917072HCID 46917072, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (100 mg, 0.336 mmol), 1-(4-chlorophenyl)piperazine dihydrochloride (100 mg, 0.367 mmol) and K2CO3 (149 mg, 1.075 mmol) in MeCN (5 mL) was heated at reflux for 24 hrs. The reaction mixture was diluted with ethyl acetate (20 mL), and the organic phase washed with water (20 mL) and then brine (20 mL), dried over MgSO4 and evaporated in vacuo. The residue was triturated with diethyl ether and dried in vacuo at 50° C. to afford 2-[4-(4-chlorophenyl)piperazin-1-yl]-N-(3-(quinoxalin-2-yl)phenyl)acetamide (56 mg, 36% yield). LCMS calculated for C26H24ClN5O (M+H): 458.17. found 458.21. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.00 (1H, br. s), 9.51 (1H, s), 8.55 (1H, m), 8.15-8.10 (2H, m), 8.05 (1H, d, 1=7.5 Hz), 7.95-7.80 (3H, m), 7.55 (1H, m), 7.21 (2H, d, J=7.5 Hz), 6.90 (2H, d, J=7.5 Hz), 3.21 (4H, m), 2.61 (4H, m).

Workup

  1. temperatureat reflux for 24 hrs
  2. washthe organic phase washed with water (20 mL)
  3. dry with materialbrine (20 mL), dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was triturated with diethyl ether
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-830807740fae46398b7efc827cf77fc8
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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