Hydrochloric Acid → 7-chloro-N-[4-(4-methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl) methyl]phenyl]quinolin-4-amine

HRID 1190866Notes

Reaction equation

HRID 1190866 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=2[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH2:4][CH2:3]1.Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30]([Cl:34])=[CH:31][CH:32]=2)[N:27]=[CH:26][CH:25]=1.Cl>C(#N)C>[Cl:34][C:30]1[CH:29]=[C:28]2[C:33]([C:24]([NH:12][C:11]3[CH:13]=[CH:14][C:8]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]4)=[C:9]([CH2:15][N:16]4[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]4)[CH:10]=3)=[CH:25][CH:26]=[N:27]2)=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 672492344-(4-Methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]aniline

Product 1

HCID 672620117-chloro-N-[4-(4-methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl) methyl]phenyl]quinolin-4-amineYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-methylpiperazin-1-yl)-3-[(4-methylpiperazin-1-yl)methyl]aniline (68 mg, 0.22 mmol) and 4,7-dichloroquinoline (44 mg, 1 eq) were refluxed overnight in 10 mL of acetonitrile with 0.66 mL of HCl 1M. The reaction mixture was then evaporated and purified by preparative thin-layer chromatography (DCM/MeOH/NH4O/18/210.1) to yield expected compound as a pale yellow solid (49 mg, 48% yield). m/z (ESI) 465.2 [M+H]+.

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by preparative thin-layer chromatography (DCM/MeOH/NH4O/18/210.1)

Sources & evidence

ORD record
ord-114b68594d80430e993e3008a697c7bf
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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