Hydrochloric Acid → HCID 60064202, compound

HRID 412618Notes

Reaction equation

HRID 412618 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH2:17][CH2:18][CH:19]2OCC[O:20]2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH2:17][CH2:18][CH:19]=[O:20])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 60064149HCID 60064149, compound

Product 1

HCID 60064202HCID 60064202, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Ethoxycarbonyl-4-[2-(1,3-dioxolan-2-yl)ethyl]piperidine-1-carboxylic acid benzyl ester (460 mg) was dissolved in tetrahydrofuran (5 ml) and thereto was dropwise added conc. hydrochloric acid (5 ml) with ice-cooling, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was poured into aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:acetone=5:1) to give the title compound (300 mg).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:acetone=5:1)

Sources & evidence

ORD record
ord-87cdf8999eca4cdca4af782ec9cde0de
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…