Sulfuric Acid → HCID 86730316, compound

HRID 1427004Notes

Reaction equation

HRID 1427004 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[O:22][CH2:23][C:24](C)(C)N=3)=[CH:17][CH:16]=2)([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:29]>C(O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:22][CH2:23][CH3:24])=[O:29])=[CH:19][CH:20]=2)([OH:14])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 68967526HCID 68967526, compound

Product 1

HCID 86730316HCID 86730316, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

1-Benzyl-4-(4-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl)piperidin-4-ol described in Production Example 7-1 (13.4 g, 36.8 mmol) was dissolved in ethanol (300 mL), then sulfuric acid was added, and the mixture was stirred at 90° C. for 12 hours. The reaction mixture was cooled to room temperature and then the solvent was evaporated under vacuum. The resultant residue was dissolved in dichloromethane, the resultant was washed with a saturated aqueous sodium bicarbonate solution, and then the organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under vacuum and the resultant residue was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1). The target fraction was concentrated under vacuum to obtain the title compound (7.23 g, 58%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under vacuum
  3. dissolutionThe resultant residue was dissolved in dichloromethane
  4. washthe resultant was washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under vacuum
  8. customthe resultant residue was purified with NH silica gel column chromatography (n-heptane:ethyl acetate=4:1-1:1)
  9. concentrationThe target fraction was concentrated under vacuum

Sources & evidence

ORD record
ord-b9d8680da755463ca73df4ff1b6dd3eb
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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