Hydrochloric Acid → HCID 43167822, compound

HRID 1091795Notes

Reaction equation

HRID 1091795 reaction equation
Cl.[N:2]1([CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>O1CCOCC1.CO>[NH:14]1[CH2:15][CH2:16][CH:11]([O:10][CH2:9][CH2:8][N:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57791789Tert-butyl 4-(2-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate

Product 1

HCID 43167822HCID 43167822, compound

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-(piperidin-1-yl)ethoxy)piperidine-1-carboxylate (114)(6.5 g, 20.80 mmol) in MeOH (16 mL) and the reaction mixture was stirred at room temperature for 6 hours. Removal of solvent afforded 1-(2-(piperidin-4-yloxy)ethyl)piperidine as its hydrochloride salt (0.540 g, 12.22%). 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 material a colourless liquid which was used without further purification; 1H NMR (400.132 MHz, CDCl3) δ 1.33-1.47 (2H, m), 1.50-1.71 (3H, m), 1.86-1.96 (4H, m), 2.50-2.67 (6H, m), 3.00-3.14 (4H, m), 3.34 (1H, septet), 3.55 (2H, t), 3.60 (2H, t).

Workup

  1. customRemoval of solvent

Sources & evidence

ORD record
ord-e02ec742a9fa4cea9f17232cfa9da56a
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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