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

HRID 2095450Notes

Reaction equation

HRID 2095450 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]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[F:27][C:24]([F:25])([F:26])[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 59371591HCID 59371591, compound

Product 1

HCID 593715824-[2-[4-(Trifluoromethyl)benzyloxy]ethyl]piperidineYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-[2-[4-(trifluoromethyl)benzyloxy]ethyl]piperidine (496 mg, 1.28 mmol) in MeOH (0.5 mL) was added 2N anhydrous HCl/ether (2.0 mL, 4.0 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-[2-[4-(trifluoromethyl)benzyloxy]ethyl]piperidine (321 mg, 87%) was obtained as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 7.56 (d, 2H, J=8.4 Hz), 7.41 (d, 2H, J=8.0 Hz), 4.51 (s, 2H), 3.50 (t, 2H, J=6.0 Hz), 3.39 (br, 1H), 3.07 (d, 2H, J=12.0 Hz), 2.59 (t, 2H, J=11.6 Hz), 1.66 (d, 2H, J=12.8 Hz), 1.54 (m, 3H), 1.20 (m, 2H).

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-96e7585f4f0f4ff2b62068381081d14a
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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