1,4-Dioxane hydrochloride → HCID 16660652, compound

HRID 1968467Notes

Reaction equation

HRID 1968467 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:35])=[C:6]([CH:34]=1)[O:7][CH2:8][C:9]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25]COC)=[CH:21][C:20]=2[O:29][CH3:30])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([CH3:33])=[CH:12][C:13]([CH3:32])([CH3:31])[NH:14]2.Cl.O1CCOCC1>O1CCOCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:35])=[C:6]([CH:34]=1)[O:7][CH2:8][C:9]1[C:18]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][C:20]=2[O:29][CH3:30])=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11]([CH3:33])=[CH:12][C:13]([CH3:31])([CH3:32])[NH:14]2

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58027129HCID 58027129, compound

Product 1

HCID 16660652HCID 16660652, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

5-(5-Fluoro-2-methylphenoxymethyl)-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-1, 424 mg, 0.888 mmol) was dissolved in 1,4-dioxane (5 mL), 4N HCl/1,4-dioxane solution (666 μL) was added thereto, and then the mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate (150 mL). The mixture was washed with water (100 mL, twice) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (241.7 mg) as a colorless solid. (Yield 63%)

Workup

  1. washThe mixture was washed with water (100 mL
  2. dry with materialtwice) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-0733041f655148ceb4c838b17bc39bb6
Source dataset
uspto-grants-2013_04
Patent number
US08426406B2

Reaction notes

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