2-(1-Piperazinylmethyl)quinoline → HCID 23296260, compound

HRID 1953474Notes

Reaction equation

HRID 1953474 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:17]2[N:18]=[N:19][N:20]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]4[CH:40]=[CH:39][C:38]5[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=5)[N:32]=4)[CH:24]=3)[N:21]=2)[C:6]1=[O:41].[N:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44][C:43]=1[CH2:52][N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1>C(Cl)(Cl)Cl.CO>[ClH:1].[ClH:1].[N:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44][C:43]=1[CH2:52][N:53]1[CH2:58][CH2:57][N:56]([CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=3)[CH:8]=[C:7]([C:17]3[N:18]=[N:19][N:20]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][C:31]5[CH:40]=[CH:39][C:38]6[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=6)[N:32]=5)[CH:24]=4)[N:21]=3)[C:6]2=[O:41])[CH2:55][CH2:54]1

Participants

4

Reactant 2

HCID 43753132-(1-Piperazinylmethyl)quinolineHCID 15481567HCID 15481567, compound

Product 1

HCID 23296260HCID 23296260, compoundYield 182.9%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(3-chloropropyl)-6-methoxy-3-{2-[3-(2-quinolylmethoxy)benzyl]tetrazolyl}quinolin-2-one (179 mg, 0.316 mmol) and N-(2-quinolylmethyl)piperazine (287 mg, 1.26 mmol) was stirred under an argon flow at 120° C. for 2.5 hours. The mixture was allowed to cool, subjected to silica gel column chromatography (developer: chloroform-methanol (40:1)), and purified. Fractions including the target compound were collected, and concentrated under reduced pressure, to thereby obtain the free base of the title compound (219 mg, 0.289 mmol) as yellow oily matter. The thus-obtained free base of the title compound was dissolved in methanol (50 ml), and a solution of hydrochloric acid (4N) in ethyl acetate (144 μl, 0.576 mmol) was added to the resultant mixture. The mixture was crystallized from a methanol-diethylether mixture, to thereby obtain the title compound (184 mg, 0.22 mmol, 70.1%) as yellow powder.

Workup

  1. temperatureto cool
  2. custompurified
  3. customwere collected
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f447097d4304f83b416389911f9ed5c
Source dataset
uspto-grants-2000_09
Patent number
US06117886

Reaction notes

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