1,4-Dioxane hydrochloride → HCID 25015626, compound

HRID 1678338Notes

Reaction equation

HRID 1678338 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9]COC)[CH:6]=[CH:5][C:4]=1[C:13]1[C:14]([CH2:26][NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH3:35])=[C:15]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18]([CH3:24])([CH3:23])[CH:17]=[C:16]2[CH3:25].Cl.O1CCOCC1>O1CCOCC1.C(OCC)(=O)C>[OH:9][C:7]1[CH:6]=[CH:5][C:4]([C:13]2[C:14]([CH2:26][NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18]([CH3:24])([CH3:23])[CH:17]=[C:16]3[CH3:25])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57990632HCID 57990632, compound

Product 1

HCID 25015626HCID 25015626, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

6-(2-Methoxy-4-methoxymethoxyphenyl)-5-(2-methoxyphenylaminomethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-1, 181 mg, 0.381 mmol) was dissolved in 1,4-dioxane (3 mL), 4N HCl/1,4-dioxane solution (1 mL) was added thereto, and then the mixture was stirred at room temperature for 2.5 hours. The mixture was diluted with ethyl acetate (30 mL), washed with saturated aqueous sodium hydrogen carbonate solution (30 mL), water (30 mL) and saturated brine (30 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 (101 mg) as a pale orange solid. (Yield 62%)

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution (30 mL), water (30 mL) and saturated brine (30 mL) successively
  2. dry with materialdried 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-183da15eac9e4f3790d6cbcd11f3f898
Source dataset
uspto-grants-2011_08
Patent number
US08008498B2

Reaction notes

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