Hydrochloric Acid → 4-(2-Methoxyethoxy)piperidine hydrochloride

HRID 751652Notes

Reaction equation

HRID 751652 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:19].O1CCOCC1>CO>[ClH:19].[CH3:18][O:17][CH2:16][CH2:15][O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57476927Tert-butyl 4-(2-methoxyethoxy)piperidin-1-carboxylate

Product 1

HCID 220613544-(2-Methoxyethoxy)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2-methoxyethoxy)-piperidine-1-carboxylic acid tert-butyl ester (Preparation 81, 114 mg, 0.44 mmol) in methanol (3 mL) was added 4M HCl in dioxane (550 μL, 2.20 mmol) and the reaction stirred at rt for 16 h. Solvent was removed in vacuo and the crude residue dissolved in water (10 mL). The aqueous solution was extracted with ethyl acetate (2×10 mL) then concentrated in vacuo. Purification by trituration in ethyl acetate gave the title compound as the hydrochloride salt. δH (CD3OD): 3.74–3.67 (1H, m), 3.64 (2H, m), 3.56 (2H, m), 3.40–2.39 (7H, m), 2.11–1.96 (2H, m), 1.93–1.83 (2H, m).

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe crude residue dissolved in water (10 mL)
  3. extractionThe aqueous solution was extracted with ethyl acetate (2×10 mL)
  4. concentrationthen concentrated in vacuo
  5. customPurification by trituration in ethyl acetate

Sources & evidence

ORD record
ord-f467755a87d641e888388f4890f434f6
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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