4-((4-Methylpiperazin-1-yl)methyl)aniline → HCID 66576789, compound

HRID 1396192Notes

Reaction equation

HRID 1396192 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:5]([CH3:15])=[CH:4][N:3]=1.[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1>C(Cl)Cl.CO>[Cl:14][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([CH3:15])=[CH:4][N:3]=[C:2]([NH:28][C:27]3[CH:26]=[CH:25][C:24]([CH2:23][N:20]4[CH2:19][CH2:18][N:17]([CH3:16])[CH2:22][CH2:21]4)=[CH:30][CH:29]=3)[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 31539964-((4-Methylpiperazin-1-yl)methyl)anilineHCID 79073950HCID 79073950, compound

Product 1

HCID 66576789HCID 66576789, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared according to synthesis procedure B described above from 2-chloro-4-(3-chlorophenyl)-5-methylpyrimidine and 4-((4-methylpiperazin-1-yl)methyl)aniline in 77% 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), 7.61 (s, 1H), 7.56 (d, 2H, J=8.2 Hz), 7.48 (m, 1H), 7.40 (m, 2H), 7.25 (d, 2H, J: not calculated due to overlapping peaks), 3.45 (s, 2H), 2.45 (bs, 8H), 2.27 (s, 3H), 2.24 (s, 3H); MS (ESI): 408.4 [M+H]+, 204.7 [M+2H]2+.

Workup

  1. customaccording to synthesis procedure B
  2. temperaturegradually increasing to 95:5)

Sources & evidence

ORD record
ord-dcccb30fe3db435cb212c8e700c68f8e
Source dataset
uspto-grants-2014_12
Patent number
US08901120B2

Reaction notes

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