Ether hydrochloride → 4-[2-(4-Fluorobenzyloxy)ethyl]piperidine

HRID 2095447Notes

Reaction equation

HRID 2095447 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]([F:24])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[F: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 593714721-(Tert-butoxycarbonyl)-4-[2-(4-fluorobenzyloxy)ethyl]piperidine

Product 1

HCID 207353244-[2-(4-Fluorobenzyloxy)ethyl]piperidineYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-[2-(4-fluorobenzyloxy)ethyl]piperidine (257 mg, 0.76 mmol) in MeOH (0.5 mL) was added 2N anhydrous HCl/ether (1.0 mL, 2.0 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 the combined organic phases were dried over Na2SO4. After evaporation, 4-[2-(4-fluorobenzyloxy)ethyl]piperidine (150 mg, 83% yield) 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 materialthe combined organic phases were dried over Na2SO4
  6. customAfter evaporation

Sources & evidence

ORD record
ord-e2b137b0d774441fac306a34da9131bc
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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