Acetic Acid → Ethyl 4-(4-oxopiperidin-1-yl)benzoate

HRID 2356047Notes

Reaction equation

HRID 2356047 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.C(O)(=O)C>C1COCC1>[O:4]=[C:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 12717439Ethyl 4-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)benzoate

Product 1

HCID 12717442Ethyl 4-(4-oxopiperidin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 158A (6.31 g, 21.7 mmol) and 30% aqueous acetic acid (100 mL) in THF (50 mL) was stirred at 95° C. for 6 hours, cooled to room temperature, concentrated, treated with water, and extracted with dichloromethane. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (DCI) m/e 248 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additiontreated with water
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c3624f870f3d4daea5a1ccfd022ea569
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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