1,4-Dioxane hydrochloride → HCID 86595273, compound

HRID 1788369Notes

Reaction equation

HRID 1788369 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH:23]=[CH:24][CH:25]=[C:26]3[CH2:31][CH2:30][N:29](C(O)=O)[CH2:28][CH2:27]3)(=[O:22])=[O:21])=[CH:16][CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.O1CCOCC1>CO>[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([S:20]([CH:23]=[CH:24][CH:25]=[C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)(=[O:21])=[O:22])=[CH:18][CH:19]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86595274HCID 86595274, compound

Product 1

HCID 86595273HCID 86595273, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.2 g (0.37 mmol) of tert-butyl ester of 4-{3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]allylidene}piperidine-1-carboxylic acid (II-24a) obtained in Example 12 (12-2) in methanol (2.0 mL) was added 4N hydrochloric acid-dioxane solution (2.0 mL) at 0° C. and stirred for 2 hours at room temperature. The reaction mixture was then concentrated under a reduced pressure, treated with saturated aqueous sodium bicarbonate, extracted with chloroform, and dried over anhydrous magnesium sulfate. After drying, the solution was filtered, and the filtrate was concentrated under a reduced pressure to give crude 2-methyl-4-[4-(3-piperidin-4-ylidene-1-propene-1-sulfonyl)phenoxymethyl]quinoline. This was dissolved in dichloromethane (10 mL), treated with triethylamine (0.077 mL, 0.56 mmol) and pivaloyl chloride (0.058 g, 0.48 mmol) at 0° C., and stirred for 2 hours. The reaction mixture was then concentrated under a reduced pressure, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and saturated brine, and dried over magnesium sulfate. The filtrate was concentrated under a reduced pressure to obtain 0.18 g (yield 94.7%) of 2,2-dimethyl-1-(4-{3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]allylidene}piperidin-1-yl)propan-1-one (X-25). Its physical property is shown below.

Workup

  1. concentrationThe reaction mixture was then concentrated under a reduced pressure
  2. additiontreated with saturated aqueous sodium bicarbonate
  3. extractionextracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter drying
  6. filtrationthe solution was filtered
  7. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-d30caf74ce65475eb4229fe1a75b1cfc
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

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