Hydrochloric Acid → 1-[(Piperidin-4-yloxy)acetyl]piperidine

HRID 1091792Notes

Reaction equation

HRID 1091792 reaction equation
Cl.[O:2]=[C:3]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1>O1CCOCC1.CO>[N:19]1([C:3](=[O:2])[CH2:4][O:5][CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57791806Tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate

Product 1

HCID 242088381-[(Piperidin-4-yloxy)acetyl]piperidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 4 N HCl solution in dioxane (6 mL) was added to a solution of tert-butyl 4-(2-oxo-2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate (111) (7.5 g, 22.98 mmol) in MeOH (20 mL) and the reaction mixture was stirred at room temperature for 6 hours. Removal of solvent afforded 1-(piperidin-1-yl)-2-(piperidin-4-yloxy)ethanone as its hydrochloride salt (2.300 g, 44.2%). This salt was then dissolved in methanol (50 ml) and MP-carbonate (14.88 g, 33.61 mmol) was added. The resulting mixture was filtered and the solvent removed to give the desired compound (2.300 g, 44.2%), which was used without further purification.

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-3b9f0a5f739846a095556e11c5c3a677
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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