HCID 86613782, compound → HCID 68690034, compound

HRID 1175213Notes

Reaction equation

HRID 1175213 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([CH:19]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH3:20])[CH:18]=1)[C:13]([O-:15])=[O:14])(=[O:3])[CH3:2]>C1COCC1.CO.O.[OH-].[Na+]>[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([CH:19]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH3:20])[CH:18]=1)[C:13]([OH:15])=[O:14])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86613782HCID 86613782, compound

Product 1

HCID 68690034HCID 68690034, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideCatalystHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 3-(1-acetylpiperidin-2-yl)-5-(1-cyclohexylethyl)benzoate (80 mg, 0.22 mmol) in THF:MeOH:water (1:1:1, 6 mL) was added NaOH (6 N, 10 drops) and the mixture was stirred for 3 h. The volatiles were removed in vacuo and the mixture was acidified with aqueous HCl (6 N) to a pH of about 2. The mixture was extracted with EtOAc (3×10 mL). The combined organics were washed with water (1×10 mL), brine (1×10 mL), dried over sodium sulfate, filtered and concentrated. The title compound was used without further purification.

Workup

  1. customThe volatiles were removed in vacuo
  2. extractionThe mixture was extracted with EtOAc (3×10 mL)
  3. washThe combined organics were washed with water (1×10 mL), brine (1×10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe title compound was used without further purification

Sources & evidence

ORD record
ord-dc0087c861244bd098742f876b722049
Source dataset
uspto-grants-2010_11
Patent number
US07838676B2

Reaction notes

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