Trifluoroacetic acid → 6-Butyl-8-(4-piperidinyloxy)quinoline

HRID 1363002Notes

Reaction equation

HRID 1363002 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:15][CH:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579260451,1-Dimethylethyl 4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinecarboxylate2×

Product 1

HCID 579260486-Butyl-8-(4-piperidinyloxy)quinolineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-[(6-butyl-8-quinolinyl)oxy]-1-piperidinecarboxylate (for example, as prepared for Intermediate 3) (21.5 g, 56 mmol) was dissolved in DCM (50 ml) and trifluoroacetic acid (50 ml) was added very slowly. The mixture was stirred at room temperature for 1 h. The solvent was evaporated to dryness and the residue treated with saturated aqueous sodium carbonate solution. The mixture was extracted with EtOAc (×2), washed with water, and dried (MgSO4). The drying agent was removed by filtration and the filtrate was evaporated to dryness (22 g). This was still a trifluoracetic acid salt and was re-dissolved in EtOAc, washed with aqueous sodium carbonate, water, and dried (MgSO4). The drying agent was removed by filtration and the filtrate was evaporated to dryness to afford the title compound (15.9 g). LCMS RT=2.45 min, ES+ve m/z 285 [M+H]+.

Workup

  1. customThe solvent was evaporated to dryness
  2. additionthe residue treated with saturated aqueous sodium carbonate solution
  3. extractionThe mixture was extracted with EtOAc (×2)
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customThe drying agent was removed by filtration
  7. customthe filtrate was evaporated to dryness (22 g)
  8. dissolutionwas re-dissolved in EtOAc
  9. washwashed with aqueous sodium carbonate, water
  10. dry with materialdried (MgSO4)
  11. customThe drying agent was removed by filtration
  12. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-cb5f49dfd25f410f8200f32818ad1e4b
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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