Hydrochloric Acid → HCID 76372213, compound

HRID 715844Notes

Reaction equation

HRID 715844 reaction equation
[F:1][C:2]1([F:54])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([O:18]CC4C=CC(OC)=CC=4)[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[CH:42]([F:53])[C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=2)[CH2:4][CH2:3]1.Cl.C(=O)([O-])O.[Na+]>O1CCOCC1>[F:54][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:28])([CH3:29])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:31][CH2:32][N:33]([C:36]4[N:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[CH2:34][CH2:35]3)[C:9]=2[CH:42]([F:53])[C:43]2[CH:44]=[CH:45][C:46]([C:49]([F:50])([F:52])[F:51])=[CH:47][CH:48]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 86682424HCID 86682424, compound

Product 1

HCID 76372213HCID 76372213, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1.28 g (1.70 mmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-[1-(pyrimidin-2-yl)piperidin-4-yl]-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 15, in 8 ml of 1,4-dioxane, 4 ml of 6 N hydrochloric acid was added, and the reaction solution was stirred at 70° C. for 3 hours. After completion of the reaction, the reaction solution was poured into saturated sodium hydrogencarbonate aqueous solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. n-Heptane was added to the obtained residue and the precipitate was obtained by filtration to provide 0.93 g of the title compound as a white solid (yield: 86%).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionn-Heptane was added to the obtained residue
  7. customthe precipitate was obtained by filtration

Sources & evidence

ORD record
ord-e1d3dbcd768e4e4f8f7531bfdf05dc7d
Source dataset
uspto-grants-2015_11
Patent number
US09187450B2

Reaction notes

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