1-Phenylpiperazine → HCID 3759112, compound

HRID 2045925Notes

Reaction equation

HRID 2045925 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+].[C:28]1([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1OCCOCCOCCOCCOCCOC1>CC#N.O>[C:28]1([N:34]2[CH2:39][CH2:38][N:37]([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])[CH2:36][CH2:35]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 3759112HCID 3759112, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A slurry of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (1.64 g, 5.5 mmol), K2CO3 (0.92 g, 6.87 mmol), 1-phenylpiperazine (1.05 mL, 5.5 mmol) and a catalytical amount of 18-crown-6 in MeCN (20 mL) was refluxed for 7 hrs, cooled to room temperature, and diluted with water. The resulting solid was filtered, washed with water, and dried to afford 2-(4-phenylpiperazin-1-yl)-N-[3-(quinoxalin-2-yl)phenyl]acetamide (2.1 g, 90% yield). LCMS calculated for C26H25N50 (M+H): 424.52. found 424. 1H-NMR (DMSO-d6, 250 Mhz) δH: 10.5 (1H, br. s), 9.52 (1H, s), 8.58 (1H, br. s), 8.20-7.80 (6H, m), 7.55 (1H, m), 7.25-7.15 (2H, m), 6.98-6.90 (2H, m), 6.80-6.72 (1H, m), 3.28-3.25 (6H, m), 2.75-2.65 (4H, m).

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-a865c17a209b4ef6b328faf0df6cb803
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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