Piperidine, 1-(2-chloroethyl)-, hydrochloride → 3-({7-Chloro-1-[2-(piperidin-1-yl)ethyl]-1,4-dihydroquinolin-4-ylidene}amino)-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile

HRID 1190901Notes

Reaction equation

HRID 1190901 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:10]=[C:11]2[C:20]3[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=3)[N:14]([CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:13]=[CH:12]2)[CH:9]=1)[C:5]#[N:6].Cl.Cl[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.CCN(C(C)C)C(C)C>CC(CC)CO>[Cl:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11](=[N:10][C:8]3[CH:7]=[C:4]([CH:3]=[C:2]([NH:1][CH2:32][CH2:33][N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[CH:9]=3)[C:5]#[N:6])[CH:12]=[CH:13][N:14]2[CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 81531DiisopropylethylamineHCID 672472943-Amino-5-({7-chloro-1-[2-(piperidin-1-yl) ethyl]-1,4-dihydroquinolin-4 ylidene}amino)benzonitrile

Product 1

HCID 683303743-({7-Chloro-1-[2-(piperidin-1-yl)ethyl]-1,4-dihydroquinolin-4-ylidene}amino)-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 87232-Methyl-1-butanolSolvent

Procedure

3-amino-5-({7-chloro-1-[2-(piperidin-1-yl)ethyl]-1,4-dihydroquinolin-4-ylidene}amino)benzonitrile prepared from example 21 (132 mg, 0.32 mmol), 1-(2-chloroethyl)piperidine hydrochloride (182 mg, 3 eq) and DIEA (0.51 mL, 9.3 eq) were refluxed in 15 mL of 2-methylbutan-1-ol for 10 h. The reaction mixture was then evaporated and the residue and was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1) to yield expected compound as a yellow oil (28 mg, 17% yield). m/z (ESI) 517.5 [M+H]+.

Workup

  1. customThe reaction mixture was then evaporated
  2. customthe residue and was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1)

Sources & evidence

ORD record
ord-246d17e0bae44081a8e50011d83dff61
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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