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Ethyl Acetate → 2-[2-(4-Methyl-piperazin-1-yl)-quinolin-4-yl]-acetamide

HRID 1169613
Notes
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Reaction equation

HRID 1169613 reaction equation
Cl[C:2]1[CH:11]=[C:10]([CH2:12][C:13]([NH2:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CCOC(C)=O>CN1CCCC1=O>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:11]=[C:10]([CH2:12][C:13]([NH2:15])=[O:14])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:19][CH2:18]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 531671-MethylpiperazineHCID 187708752-Chloro-4-quinolineacetamide

Product 1

HCID 187708612-[2-(4-Methyl-piperazin-1-yl)-quinolin-4-yl]-acetamide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

2-(2-chloro-quinolin-4-yl)-acetamide (500 mg, 2.27 mmol) is dissolved in 1-methyl-2-pyrrolidinone (3.0 mL). N-methylpiperazin (1.3 mL, 5 eq.) is added and the reaction is stirred at 80° C. for 48 h. AcOEt (20 mL) is added and the precipitate is purified by FCC (AcOEt/EtOH/28% NH4OH 80:18:1) to afford 2-[2-(4-methyl-piperazin-1-yl)-quinolin-4-yl]-acetamide as a solid.

Workup

  1. customthe precipitate is purified by FCC (AcOEt/EtOH/28% NH4OH 80:18:1)

Sources & evidence

ORD record
ord-a0e3d006b79140fb804bb1e0fee2aa3f
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07825124B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes