Hydrochloric Acid → HCID 68789286, compound

HRID 1913884Notes

Reaction equation

HRID 1913884 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:17](=[O:29])[CH2:16][CH2:15]4)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[ClH:30]>C(OCC)(=O)C.C(O)C>[ClH:30].[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([O:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][CH:21]=3)[N:18]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:17](=[O:29])[CH2:16][CH2:15]4)[CH2:9][CH2:10]2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 46866223HCID 46866223, compound

Product 1

HCID 68789286HCID 68789286, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 6-[(1-cyclobutylpiperidin-4-yl)oxy]-1-(4-fluorophenyl)-3,4-dihydroquinolin-2(1H)-one (Compound No. 60) prepared in Example 6 (0.90 g) in a mixture of ethyl acetate (10 mL) and ethanol (2 mL), 4N hydrochloric acid in ethyl acetate (1.14 mL) was added and stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, followed by addition of isopropanol (7 mL) and ethanol (2 mL) to the residue. The mixture was stirred for 5 minutes while heating in an oil bath (110° C.), and then stirred while cooling to room temperature. The precipitate was collected by filtration and dried to give the titled compound (0.93 g, 95%) as a colorless crystal.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionfollowed by addition of isopropanol (7 mL) and ethanol (2 mL) to the residue
  4. stirringThe mixture was stirred for 5 minutes
  5. temperaturewhile heating in an oil bath (110° C.)
  6. stirringstirred
  7. temperaturewhile cooling to room temperature
  8. filtrationThe precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-97704a19ab1d4cb184a50ea9718b5335
Source dataset
uspto-grants-2013_12
Patent number
US08609847B2

Reaction notes

Loading…