1-Methylpiperazine → HCID 46916408, compound

HRID 2045926Notes

Reaction equation

HRID 2045926 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].[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C(O)C>[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([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])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 14854332-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide

Product 1

HCID 46916408HCID 46916408, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-N-(3-quinoxalin-2-ylphenyl)acetamide (100 mg, 0.336 mmol) and N-methylpiperazine (79 μL, 0.706 mmol) in ethanol (5 mL) was heated at 100° C. for 18 hrs. The solvent was evaporated and the oily residue was submitted to preparative LCMS to afford 2-(4-methylpiperazin-1-yl)-N-[3-(quinoxalin-2-yl)phenyl]acetamide (42 mg, 34%). LCMS calculated for C21H23N5O (M+H): 362.19. found 362.16. 1H-NMR (DMSO-d6, 400 Mhz) δH: 9.90 (1H, br. s), 9.51 (1H, s), 8.54 (1H, m), 8.19-8.12 (2H, m), 8.08 (1H, d, J=7 Hz), 7.94-7.82 (3H, m), 7.55 (1H, m), 3.18 (2H, s), 2.60-2.53 (4H, br), 2.48-2.40 (4H, br), 2.20 (3H, s).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3e38fb5c4ec742168b6570c292690010
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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