Hydrochloric Acid → HCID 68576681, compound

HRID 272970Notes

Reaction equation

HRID 272970 reaction equation
[OH-].[Na+].[CH:3]1([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4([C:26]([O:28]CC)=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4]1.Cl>O1CCOCC1.O>[CH:3]1([N:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 68575805HCID 68575805, compound

Product 1

HCID 68576681HCID 68576681, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydroxide (200 mg, 5 mmol) was added to a solution of ethyl 4-{4-[(1-cyclobutylpiperidin-4-yl)oxy]phenyl}tetrahydro-2H-pyran-4-carboxylate (870 mg, 2.25 mmol) in dioxane (10 ml) and water (2 ml). The reaction mixture was heated to reflux for 16 hours under nitrogen. The reaction was not complete. More sodium hydroxide (190 mg, 4.75 mmol) in water (4 ml) was added and the reaction heated at reflux for 18 hours. 2N Hydrochloric acid (5 ml, 9.75 mmol) was added and the mixture concentrated in vacuo to a white powder (2.0 g) containing the title compound and sodium chloride. LRMS APCI+ m/z 360 [MH]+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours under nitrogen
  3. temperaturethe reaction heated
  4. temperatureat reflux for 18 hours
  5. concentrationthe mixture concentrated in vacuo to a white powder (2.0 g)
  6. additioncontaining the title compound and sodium chloride

Sources & evidence

ORD record
ord-8fd5ee38531348908533ef4cc4b13d6f
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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