Hydrochloric Acid → 6-Pentyl-8-(4-piperidinyloxy)quinoline

HRID 1363006Notes

Reaction equation

HRID 1363006 reaction equation
[CH2:1]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([O:16][CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH3:5].Cl>O1CCOCC1>[CH2:1]([C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([O:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 669215051,1-Dimethylethyl 4-[(6-pentyl-8-quinolinyl)oxy]-1-piperidinecarboxylate2×

Product 1

HCID 669217016-Pentyl-8-(4-piperidinyloxy)quinolineYield 114.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

1,1-Dimethylethyl 4-[(6-pentyl-8-quinolinyl)oxy]-1-piperidinecarboxylate (for example, as prepared for Intermediate 7) (2.20 g, 5.52 mmol) was dissolved in dioxane (10 ml) and the solution was treated with a solution of hydrogen chloride in dioxane (4M, 12.5 ml). The mixture was stirred under nitrogen overnight at room temperature, and then concentrated in vacuo. The residue was applied to a SCX-2 ion exchange cartridge (70 g) which had been preconditioned with methanol. The cartridge was washed with methanol, and then eluted with 10% aqueous 0.88 s.g. ammonia in methanol. The relevant basic fractions were concentrated in vacuo to give the title compound (1.88 g); LCMS RT=2.70 min, ES+ve m/z 299 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. washThe cartridge was washed with methanol
  3. washeluted with 10% aqueous 0.88 s
  4. concentrationThe relevant basic fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-ecafe25789d24f739f7af9ed53019dfa
Source dataset
uspto-grants-2011_02
Patent number
US07884114B2

Reaction notes

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