Piperazine → HCID 46916506, compound

HRID 2045941Notes

Reaction equation

HRID 2045941 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].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CC#N>[N:22]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])[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 46916506HCID 46916506, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A slurry of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (100 mg, 0.336 mmol) and piperazine (58 mg, 0.672 mmol) in MeCN (5 mL) was heated at reflux for 48 hrs. The resulting precipitate was filtrated, washed with MeCN (10 mL) and submitted to preparative LCMS to afford 2-(piperazin-1-yl)-N-(3-(quinoxalin-2-yl)phenyl)acetamide (46 mg, 39% yield). LCMS calculated for C20H21N5O (M+H): 348.42. found 348. 1H-NMR (DMSO-d6, 400 Mhz) δH: 9.92 (1H, br.), 9.52 (1H, s), 8.55 (1H, m), 8.13-8.20 (2H, m), 8.05-8.08 (1H, m), 7.82-7.98 (3H, m), 7.55-7.60 (1H, m), 3.25-3.40 (NH and 6H, br.), 2.80-2.88 (4H, br.).

Workup

  1. temperatureat reflux for 48 hrs
  2. filtrationThe resulting precipitate was filtrated
  3. washwashed with MeCN (10 mL)

Sources & evidence

ORD record
ord-6c454742ae074821b1d7ac83a2c6ba43
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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