1,4-Dioxane hydrochloride → 4-[2-(3-Pyridylmethoxy)ethyl]piperidine

HRID 2095387Notes

Reaction equation

HRID 2095387 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:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>O1CCOCC1>[N:20]1[CH:21]=[CH:22][CH:23]=[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:19]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59371585tert-Butyl 4-(2-(pyridin-3-ylmethoxy)ethyl)piperidine-1-carboxylate

Product 1

HCID 593713854-[2-(3-Pyridylmethoxy)ethyl]piperidineYield 35.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-[2-(3-pyridylmethoxyl)ethyl]piperidine (413 mg, 1.29 mmol) in dioxane (0.2 mL) was added 4N HCl/dioxane (1 mL, 4.0 mmol). The solution 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-(3-pyridylmethoxy)ethyl]piperidine (100 mg, 35%) was obtained as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.40 (m, 2H), 7.53 (d, 1H, J=7.6 Hz), 7.14 (m, 1H), 4.37 (s, 2H), 3.40 (t, 2H, J=6.0 Hz), 2.91 (d, 2H, J=12.0 Hz), 2.45 (t, 2H, J=11.6 Hz), 2.27 (s, 1H), 1.52 (d, 2H, J=12.4 Hz), 1.43 (m, 3H), 1.01 (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 materialthe combined organic phases were dried over Na2SO4
  6. customAfter evaporation

Sources & evidence

ORD record
ord-f6517d41b9ab4f26bb8cff015190b353
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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