Acetic Acid → HCID 10275841, compound

HRID 2223886Notes

Reaction equation

HRID 2223886 reaction equation
[C:1]1([CH3:34])[CH:6]=[CH:5][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][C:30]([O:32]C)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:3][CH:2]=1.O.[OH-].[Li+].O1CCOCC1.C(O)(=O)C>O>[C:1]1([CH3:34])[CH:6]=[CH:5][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][C:30]([OH:32])=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 10115897HCID 10115897, compound

Product 1

HCID 10275841HCID 10275841, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To methyl [1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetate (0.5241 g) and lithium hydroxide monohydrate (0.94 g) were added 1,4-dioxane (20 mL) and water (5 mL). The resulting suspension was stirred at room temperature for 3 days. The reaction solution was brought to dryness and the residue was diluted with water. Acetic acid (1.0 mL) was then added to the solution and it was extracted with 25% ethanol/chloroform. The extract was dried over (MgSO4) and the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography (silica gel, 10% methanol/chloroform) to give the title compound (0.36 g), which was then converted to its hydrochloride by hydrochloric acid to give the title compound as a white solid (0.3805 g).

Workup

  1. extractionwas extracted with 25% ethanol/chloroform
  2. dry with materialThe extract was dried over (MgSO4)
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting residue was purified by chromatography (silica gel, 10% methanol/chloroform)

Sources & evidence

ORD record
ord-4b56e594ccbb4a688a8c7a9ed1f0a70b
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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