4-(4-Methylpiperazin-1-yl)aniline → (4Z)-4-({[4-(4-Methyl-1-piperazinyl)phenyl]amino}methylene)-1,4-dihydro-3(2H)-isoquinolinone

HRID 2236582Notes

Reaction equation

HRID 2236582 reaction equation
C[N:2](/[CH:4]=[C:5]1/[C:6](=[O:15])[NH:7][CH2:8][C:9]2[C:14]/1=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:3].[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27]C(N)=[CH:25][CH:24]=2)[CH2:19][CH2:18]1>C1(C)C=CC=CC=1>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:28]=[CH:27][C:3]([NH:2]/[CH:4]=[C:5]3\[C:6](=[O:15])[NH:7][CH2:8][C:9]4[C:14]\3=[CH:13][CH:12]=[CH:11][CH:10]=4)=[CH:25][CH:24]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 68694591(4E)-4-[(Dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone

Product 1

HCID 46183390(4Z)-4-({[4-(4-Methyl-1-piperazinyl)phenyl]amino}methylene)-1,4-dihydro-3(2H)-isoquinolinoneYield 25.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A toluene (3 mL) solution containing (4E)-4-[(dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone (300 mg, 1.48 mmol) and 4-(4-methyl-piperazin-1-yl) -phenylamine (318 mg, 1.66 mmol) is heated at 110° C. for 4 h. Using the same workup as example 1, 0.13 g (25%) orange solid is obtained: mp 186-187° C. (dec.); HRMS (ESI) m/z calcd for C21H24N4O 349.20229. found 349.20180 (M+H)+1.

Sources & evidence

ORD record
ord-92a199a44b9b467e81d082e40a2cc0ba
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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