4-(4-Methylpiperazin-1-yl)aniline → HCID 178480732, compound

HRID 2236601Notes

Reaction equation

CO[CH:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[C:7](=[O:17])[NH:6][C:5]1=[O:18].[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=2)[CH2:22][CH2:21]1>CN(C)C=O>[CH3:19][N:20]1[CH2:21][CH2:22][N:23]([C:26]2[CH:31]=[CH:30][C:29]([NH:32]/[CH:3]=[C:4]3\[C:5](=[O:18])[NH:6][C:7](=[O:17])[C:8]4[C:13]\3=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=4)=[CH:28][CH:27]=2)[CH2:24][CH2:25]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-methoxymethylene-1,3-dioxo-1,2,3,4-tetrahydro-isoquinoline-6-carboxylic acid (90 mg, 0.364 mmol), 4-(4-methyl-piperazin-1-yl)-phenylamine (69.6 mg, 0.364 mmol) in 1 mL of N,N-dimethylformamide is heated at 100° C. for 1 h. After cooling in the refrigerator, the precipitate is collected, and washed with ether to give 96 mg (65%) of yellow solid mp 278-280° C.; HRMS (ESI) m/z calcd for C22H22N4O4 407.17139. found 407.17128 (M+H)+1, Analysis for C22H22N4O4, Calcd: C, 63.60; H, 5.58; N, 13.49. Found: C, 63.67; H, 5.98; N, 13.20.

Workup

temperatureAfter cooling in the refrigerator
customthe precipitate is collected
washwashed with ether

Sources & evidence

ORD record: ord-c732a8c458cd4af48dc1a5af4b00303e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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