Triethylamine → 6-Bromo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

HRID 2112819Notes

Reaction equation

HRID 2112819 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[Br:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21](Cl)[CH:20]=[C:19]2[CH3:27]>O1CCOCC1>[Br:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([N:5]1[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]1)[CH:20]=[C:19]2[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 693814-MethylpiperidineHCID 47381436-Bromo-2-chloro-4-methylquinoline

Product 1

HCID 690634506-Bromo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.24 mL (2.0 mmol) of 4-methylpiperidine and 0.28 mL (2.0 mmol) of triethylamine are added to a solution of 0.51 g (2.0 mmol) of 6-bromo-2-chloro-4-methylquinoline in 15 mL of 1,4-dioxane and the reaction mixture is refluxed overnight. After cooling, the precipitate is filtered off, the filtrate is evaporated down, the residue is combined with acetonitrile and MTBE, filtered to remove insoluble ingredients, and the filtrate is evaporated down again. Yield: 0.69 g (100% of theoretical); C16H19BrN2 (M=319.240); calc.: molpeak (M+H)+: 319/321 (Br); found: molpeak (M+H)+: 319/321 (Br); HPLC-MS: 4.7 min (method B).

Workup

  1. temperaturethe reaction mixture is refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe precipitate is filtered off
  4. customthe filtrate is evaporated down
  5. filtrationfiltered
  6. customto remove insoluble ingredients
  7. customthe filtrate is evaporated down again
  8. custom4.7 min (method B)

Sources & evidence

ORD record
ord-1b8b9590f43a45e79841eccd17cf8b5f
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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