Hydrochloric Acid → 6-Fluoro-2-methyl-5-(1-piperazinyl)quinoline

HRID 2373600Notes

Reaction equation

HRID 2373600 reaction equation
Cl.CC([CH:6]1[CH2:11][N:10]([C:12]2[C:21]([F:22])=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16]([CH3:23])=[N:17]3)[CH2:9][CH2:8][N:7]1C([O-])=O)(C)C>O1CCOCC1>[F:22][C:21]1[C:12]([N:10]2[CH2:9][CH2:8][NH:7][CH2:6][CH2:11]2)=[C:13]2[C:18](=[CH:19][CH:20]=1)[N:17]=[C:16]([CH3:23])[CH:15]=[CH:14]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866084411,1-Dimethylethyl-4-(6-fluoro-2-methyl-5-quinolinyl)-1-piperazinecarboxylate

Product 1

HCID 574443146-Fluoro-2-methyl-5-(1-piperazinyl)quinolineYield 156.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of hydrogen chloride in dioxane (4M, 4 mL) was added to a solution of 1,1-dimethylethyl-4-(6-fluoro-2-methyl-5-quinolinyl)-1-piperazinecarboxylate (0.178 g) in dioxane (4 mL) at 0° C. The resulting mixture was warmed to room temperature and stirred for 15 h. The mixture was concentrated in vacuo and partitioned between aqueous sodium hydroxide solution and DCM. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to afford the title compound (198 mg, 100% yield).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompartitioned between aqueous sodium hydroxide solution and DCM
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-83a3fa20bad24209b7ff860d44b634b8
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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