Trifluoroacetic acid → 2-Methyl-4-(piperazin-1-yl)quinoline

HRID 333931

Reaction equation

HRID 333931 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 17750604HCID 17750604, compound

Product 1

HCID 7023182-Methyl-4-(piperazin-1-yl)quinolineYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 4-(2-methyl-4-quinolyl)piperazine-1-carboxylate (4.382 g, 13.38 mmol) was added 40 ml of a 1:1 mixture of dichloromethane and trifluoroacetic acid. The mixture was stirred at room temperature for 15 minutes. The mixture was evaporated to dryness under reduced pressure and the residue dissolved in dichloromethane. The solution was washed with 5% sodium bicarbonate solution and 3M NaOH was added until the aqueous phase remained basic. The phases were separated, the aqueous phase was extracted twice with dichloromethane, the combined organic phases were washed with saturated sodium carbonate solution, water, dried over magnesium sulfate and evaporated to dryness. 2.1 g of a solid were obtained (9.25 mmol, 69%). MS (APCI): m/z=227.8 [M+1]+.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. washThe solution was washed with 5% sodium bicarbonate solution and 3M NaOH
  4. additionwas added until the aqueous phase
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted twice with dichloromethane
  7. washthe combined organic phases were washed with saturated sodium carbonate solution, water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-bf15a9d46a7c4c29886ad66135f841f3
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Linked notes

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