Quinoline → HCID 9842061, compound

HRID 720396Notes

Reaction equation

HRID 720396 reaction equation
[Br-].[N:2]1([C:7]2[CH:25]=[CH:24][C:10]([C:11](=[O:23])[CH2:12][N+:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.BrCC(C1C=C[C:33]([N:36]2CCCC2)=[CH:32][CH:31]=1)=O.N1C2C(=CC=CC=2)C=CC=1>C(#N)C>[C:33]([C:32]1[CH:31]=[C:12]([C:11](=[O:23])[C:10]2[CH:9]=[CH:8][C:7]([N:2]3[CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:25][CH:24]=2)[N:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=12)#[N:36]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 36817854-(Pyrrolidin-1-yl)phenacyl bromideHCID 21892109HCID 21892109, compound

Product 1

HCID 9842061HCID 9842061, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4-Pyrrolidin-1-yl-phenacyl)-quinolinium bromide: A stirred solution of 2-bromo-1-(4-pyrrolidin-1-yl-phenyl)-ethanone (689 mg, 2.57 mmol), quinoline (250 μL, 2.11 mmol) and acetonitrile (5.0 mL) was refluxed at 96° C. for 7 h under argon. The solution was equilibrated to room temperature and the precipitate was filtered on a Buchner funnel. The solid was dried in vacuo to yield 812 mg (96%) of the title compound. 1H NMR (DMSO-d6): 9.49 (d, J=4.67 Hz, 1H), 9.42 (d, J=8.25 Hz, 1H), 8.54 (d, J=8.24 Hz, 1H), 8.30 (m, 2H), 8.22 (td, J=7.92, 1.31 Hz, 1H), 8.06 (t, J=7.41 Hz, 1H), 7.96 (d, J=8.79 Hz, 2H), 6.84 (s, 2H), 6.72 (d, J=9.07 Hz, 2H), 3.40 (t, J=6.31 Hz, 4H), 2.02 (t, J=6.46 Hz, 4H).

Workup

  1. customwas equilibrated to room temperature
  2. filtrationthe precipitate was filtered on a Buchner funnel
  3. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-0f83fcb3b954434cb7a265029378d581
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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