Ether hydrochloride → HCID 53410149, compound

HRID 2095418Notes

Reaction equation

HRID 2095418 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16](=[O:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[C:18]1([CH2:17][C:16]([O:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 59371432HCID 59371432, compound

Product 1

HCID 53410149HCID 53410149, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-[(phenylacetoxy)methyl]piperidine (318 mg, 0.95 mmol) in MeOH (0.2 mL) was added 2N anhydrous HCl/ether (1.5 mL, 3.0 mmol). The reaction mixture was stirred overnight. After evaporation, the residue was dissolved in deionized water. EtOAc was used to wash the aqueous layer before the pH was altered to approx. 9-10. The aqueous layer was extracted three times with CH2Cl2 and dried over Na2SO4. After evaporation, 4-[(phenylacetoxy)methyl]piperidine (173 mg, 78%) was obtained as a colorless oil.

Workup

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in deionized water
  3. washto wash the aqueous layer before the pH
  4. extractionThe aqueous layer was extracted three times with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation

Sources & evidence

ORD record
ord-2c26067b1b8f4107bf924b4dba5151d3
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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