4-(4-Methylpiperazin-1-yl)aniline → HCID 178480745, compound

HRID 2236635Notes

Reaction equation

HRID 2236635 reaction equation
CO[CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[CH:12]=2)[C:7](=[O:23])[NH:6][C:5]1=[O:24].[CH3:25][N:26]1[CH2:31][CH2:30][N:29]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[CH2:28][CH2:27]1>CN(C)C=O>[CH3:25][N:26]1[CH2:27][CH2:28][N:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][CH:3]=[C:4]3[C:13]4[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][CH2:16][N:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)[CH:12]=4)[C:7](=[O:23])[NH:6][C:5]3=[O:24])=[CH:34][CH:33]=2)[CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 68690990HCID 68690990, compound

Product 1

HCID 178480745HCID 178480745, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-methoxymethylene-6-(2-morpholin-4-yl-ethoxy)-4H-isoquinoline-1,3-dione (115 mg, 0.35 mmole), N,N-dimethylformamide (1 mL) and 4-(4-methyl-piperazin-1-yl)-phenylamine (66 mg, 0.35 mmole) is stirred and heated at 110° C. for one hour, cooled in the refrigerator. The reaction mixture is evaporated to dryness, taken up in 5% methanol in chloroform and passed through a short pad of Florisil eluting with 5% methanol in chloroform. The eluate is evaporated in vacuo and treated with ether, filtered and dried to give a yellow solid 72 mg (42%), mp 142-143° C.; MS (ES+): m/z 492.2 (M+H).

Workup

  1. temperaturecooled in the refrigerator
  2. customThe reaction mixture is evaporated to dryness
  3. customThe eluate is evaporated in vacuo
  4. additiontreated with ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-e5d6ffb3a5ba4cad841c4a44b7f916c7
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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