Quinoline → HCID 10063683, compound

HRID 720420Notes

Reaction equation

HRID 720420 reaction equation
[Cl-].[N:2]1([C:8](=[O:20])[CH2:9][N+:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.ClCC(N1CCOCC1)=O.[N:31]1C2C(=CC=CC=2)[CH:34]=[CH:33][CH:32]=1>C(#N)C>[C:32]([C:33]1[CH:34]=[C:9]([C:8]([N:2]2[CH2:7][CH2:6][O:5][CH2:4][CH2:3]2)=[O:20])[N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:11]=12)#[N:31]

Participants

5

Reactant 3

HCID 7047QuinolineHCID 74040Morpholine, 4-(chloroacetyl)-HCID 21892153HCID 21892153, compound

Product 1

HCID 10063683HCID 10063683, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Morpholin-4-yl-2-oxo-ethyl)-quinolinium chloride: A stirred solution of 2-chloro-1-morpholin-4-yl-ethanone (1.02 g, 6.23 mmol), quinoline (700 μL, 5.91 mmol) and acetonitrile (15.0 mL) was refluxed at 96° C. for 6 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 349 mg (29%) of the title compound. 1H NMR (DMSO-d6): 9.58 (d, J=6.0 Hz, 1H), 9.42 (d, J=8.1 Hz, 1H), 8.53 (d, J=7.8 Hz, 1H), 8.44 (d, J=9.0 Hz, 1H), 8.28 (m, 2H), 8.06 (t, J=7.8 Hz, 1H), 3.82 (t, J=4.2 Hz, 2H), 3.65 (m, 4H), 3.47 (t, J=4.8 Hz, 2H).

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-c0485ada04be448aad4abe687e6d7720
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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