Hydrochloric Acid → HCID 66780541, compound

HRID 1427006Notes

Reaction equation

HRID 1427006 reaction equation
[OH-].[Na+].[N:3]1([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4]1.Cl>O1CCCC1.CO.C(OCC)(=O)C>[N:3]1([CH:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71192981HCID 71192981, compound

Product 1

HCID 66780541HCID 66780541, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A 5 M sodium hydroxide solution (15 mL, 75.0 mmol) was added to a solution of methyl 4-(4-(pyrrolidin-1-yl)piperidin-1-yl)benzoate described in Production Example 8-1 (2.06 g, 7.14 mmol) in tetrahydrofuran (10 mL) and methanol (10 mL). The reaction liquid was stirred at 50° C. for 4 hours. The reaction liquid was cooled to 0° C. and then 5 M hydrochloric acid was dripped until pH reached 1. The liquid mixture was diluted with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum to obtain the title compound (1.61 g, 82%).

Workup

  1. customThe reaction liquid
  2. customThe reaction liquid
  3. temperaturewas cooled to 0° C.
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ede48b411a1a48178a4f9f502fca4f2f
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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