Ether hydrochloride → 4-(4-Phenylbutyl)piperidine

HRID 2095424Notes

Reaction equation

HRID 2095424 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][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][CH2:16][CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 538430051-(Tert-butoxycarbonyl)-4-(4-phenylbutyl)piperidine

Product 1

HCID 221110404-(4-Phenylbutyl)piperidineYield 60.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(4-phenylbutyl)piperidine (202 mg, 636 μmol) in MeOH (1 mL) was added 2N anhydrous HCl/ether (1.5 mL, 3.0 mmol). The solution was stirred overnight and then evaporated. 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-(4-phenylbutyl)piperidine (83.4 mg, 60%) was obtained as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 7.28 (m, 2H), 7.18 (m, 3H), 3.05 (m, 2H), 2.57 (m, 4H), 2.41 (br, 1H), 1.61 (m, 3H), 1.25 (m, 8H).

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 materialdried over Na2SO4
  6. customAfter evaporation

Sources & evidence

ORD record
ord-5f0114cbcd0445179cbb5f20d2841e54
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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