Hydrochloric Acid → 4-Methoxypiperidine hydrochloride

HRID 1693388Notes

Reaction equation

HRID 1693388 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:16]>CO.O1CCOCC1.O>[ClH:16].[CH3:15][O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21955381Tert-butyl 4-methoxypiperidine-1-carboxylate

Product 1

HCID 115428134-Methoxypiperidine hydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-methoxypiperidine-1-carboxylic acid tert-butyl ester (Preparation 67, 1.58 g, 7.34 mmol) in methanol (20 mL) was added hydrochloric acid in 1,4-dioxane (4M, 10 mL) and the mixture stirred for 3 h at rt. Concentration in vacuo gave an oil which was redissolved in water (100 mL). The aqueous layer was washed with ethyl acetate (2×30 mL) and concentrated to give the title compound as colourless solid. δH (D2O): 1.80, 2.14 (4H, 2m), 3.13 (2H, m), 3.38 (2H, m), 3.40 (3H, s), 3.68 (m, 1H).

Workup

  1. concentrationConcentration in vacuo
  2. customgave an oil which
  3. washThe aqueous layer was washed with ethyl acetate (2×30 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-16d3a31cdcd945869f6956ffe971671f
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

Loading…