Ether hydrochloride → HCID 56829959, compound

HRID 2095444Notes

Reaction equation

HRID 2095444 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:16][CH2:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 59371348HCID 59371348, compound

Product 1

HCID 56829959HCID 56829959, compoundYield 445.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-[2-(4-chlorobenzyloxy)ethyl]piperidine (760 mg, 0.47 mmol) in MeOH (0.5 mL) was added 2N anhydrous HCl/ether (1.5 mL, 3.0 mmol). The reaction mixture was stirred overnight, then evaporated, and 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 the combined organic phases were dried over Na2SO4. After evaporation, 4-[2-(4-chlorobenzyloxy)ethyl]piperidine (531 mg, 97%) was obtained as a colorless oil.

Workup

  1. customevaporated
  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 materialthe combined organic phases were dried over Na2SO4
  6. customAfter evaporation

Sources & evidence

ORD record
ord-b1b1094b90ee4ad4809e5c867674966e
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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