Hydrochloric Acid → HCID 86709381, compound

HRID 2172205Notes

Reaction equation

HRID 2172205 reaction equation
Cl.O1CCCCC1[O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30]([F:33])([F:32])[F:31])=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:32][C:30]([F:31])([F:33])[O:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][CH2:19][N:14]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:9]([OH:8])[C:10]=3[CH2:11][CH2:12][CH2:13]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86709382HCID 86709382, compound

Product 1

HCID 86709381HCID 86709381, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1 N hydrochloric acid aqueous solution (10 ml) was added to an ethanol solution (15 ml) of 5-(tetrahydropyran-2-yloxy)-1-[3-(4-trifluoromethoxyphenoxy)propyl]-1,2,3,4-tetrahydroquinoline (1.71 g) and stirred at room temperature overnight. A saturated sodium hydrogen carbonate aqueous solution was added thereto, and the mixture was concentrated under reduced pressure. The residue was subjected to extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to afford the title compound as a colorless oil (0.62 g).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe residue was subjected to extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-8e435d9db6e0404d9a6b972073e56046
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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