1,4-Dioxane hydrochloride → 8-(1-Piperazinyl)-5-(trifluoromethyl)quinoline

HRID 2241997Notes

Reaction equation

HRID 2241997 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2.Cl.O1CCOCC1>O1CCOCC1>[N:13]1([C:10]2[CH:11]=[CH:12][C:3]([C:2]([F:27])([F:1])[F:26])=[C:4]3[C:9]=2[N:8]=[CH:7][CH:6]=[CH:5]3)[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59204861Tert-butyl 4-[5-(trifluoromethyl)-8-quinolinyl]-1-piperazine-carboxylate

Product 1

HCID 592048478-(1-Piperazinyl)-5-(trifluoromethyl)quinolineYield 103.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-[5-(trifluoromethyl)-8-quinolinyl]-1-piperazine-carboxylate (Step 2, 0.85 g) in 5 mL dioxane was added 5 mL of 4 N HCl/dioxane. The mixture was stirred at room temperature overnight. The reaction was concentrated on a rotary evaporator, dissolved in water, neutralized with aqueous sodium hydroxide and extracted with CH2Cl2 The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated on a rotary evaporator to give 0.65 g of the desired product as an off-white solid; MP. 155-157° C.; MS (ES) m/z (relative intensity): 282 (M+H)+ (100).

Workup

  1. concentrationThe reaction was concentrated on a rotary evaporator
  2. dissolutiondissolved in water
  3. extractionextracted with CH2Cl2 The combined organic layers
  4. dry with materialwere dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-00a9dae80a0148e2a7126a7454dea24f
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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