4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576945, compound

HRID 1396193Notes

Reaction equation

HRID 1396193 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([CH3:16])=[C:12]([CH:15]=2)[C:13]#[N:14])[C:5]([CH3:17])=[CH:4][N:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1>C(Cl)Cl.CO>[CH3:16][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[C:5]([CH3:17])=[CH:4][N:3]=[C:2]([NH:30][C:29]3[CH:28]=[CH:27][C:26]([CH2:25][N:22]4[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]4)=[CH:32][CH:31]=3)[N:7]=2)=[CH:15][C:12]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 86673362HCID 86673362, compound

Product 1

HCID 66576945HCID 66576945, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from 5-(2-chloro-5-methylpyrimidin-4-yl)-2-methylbenzonitrile and 4-((4-methylpiperazin-1-yl)methyl)aniline in 93% yield (yellow solid). After flash chromatography (CH2Cl2/CH3OH 99:1 gradually increasing to 95:5). 1H NMR (400 MHz, CDCl3): δ 8.31 (s, 1H), 7.88 (d, 1H, J=1.7 Hz), 7.76 (dd, 1H, J=8.0, 1.9 Hz), 7.55 (d, 2H, J=8.6 Hz), 7.43 (d, 1H, J=7.9 Hz), 7.25 (d, 2H, J: not calculated due to overlapping peaks), 3.45 (s, 2H), 2.62 (s, 3H), 2.45 (bs, 8H), 2.26 (s, 3H), 2.25 (s, 3H); MS (ESI): 413.5 [M+H]+, 207.4 [M+2H]2+.

Workup

  1. customaccording to synthesis procedure B

Sources & evidence

ORD record
ord-0689f86e9a1f4937b085aaaaa04a671d
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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