1-Methylpiperazine → 6-Methoxy-4-(4-methyl-1-piperazinyl)-1(2H)-isoquinolinone

HRID 1852245Notes

Reaction equation

HRID 1852245 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](=[O:14])[NH:4][CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>C(O)CO>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5](=[O:14])[NH:4][CH:3]=[C:2]2[N:19]1[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 579564624-Bromo-6-methoxyisoquinolin-1(2H)-one

Product 1

HCID 709790426-Methoxy-4-(4-methyl-1-piperazinyl)-1(2H)-isoquinolinoneYield 59.5%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

To a solution of 4-bromo-6-methoxyisoquinolin-1(2H)-one (0.25 g, 0.984 mmol) and 1-methylpiperazine (0.197 g, 1.968 mmol) in ethylene glycol (2 ml) was added DIPEA (0.516 ml, 2.95 mmol). The reaction was irradiated in microwave at 140° C. for 1 h. The reaction mixture was adsorbed on silica was purified by silica gel chromatography (30% ethyl acetate in pet ether) to get the desired compound (0.16 g, 53.5%) as solid. MS: MS m/z 274.18 (M++1).

Workup

  1. customThe reaction was irradiated in microwave at 140° C. for 1 h
  2. customwas purified by silica gel chromatography (30% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-385bc6183bd04324945fe6e611708ffc
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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