Perchloric Acid → Methyl 4-(piperidin-2-yl)butanoate hydrochloride

HRID 1645247Notes

Reaction equation

HRID 1645247 reaction equation
[Cl:1](O)(=O)(=O)=O.C(OC([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=O)(C)(C)C>O1CCOCC1.O>[ClH:1].[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 57904248Tert-butyl 2-(4-methoxy-4-oxobutyl)piperidine-1-carboxylate

Product 1

HCID 66772062Methyl 4-(piperidin-2-yl)butanoate hydrochlorideYield 372.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Perchloric acid (4.96 ml, 57.4 mmol) was added to a solution of 3 (56.02 g, 287 mmol) in dioxane (1124 ml) and H2O (856 ml) and the reaction mixture was stirred at 50° C. overnight. The reaction mixture was concentrated to half its volume and aqueous saturated NaHCO3 was added. The H2O layer was extracted with CH2Cl2 (2×) and the combined organic layer was washed with brine, dried (Na2SO4) and concentrated. Purification by column chromatography (silica, heptane/EtOAc, 2:3->1:2) yielded 4 (47.45 g, 78%).

Workup

  1. concentrationThe reaction mixture was concentrated to half its volume and aqueous saturated NaHCO3
  2. additionwas added
  3. extractionThe H2O layer was extracted with CH2Cl2 (2×)
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica, heptane/EtOAc, 2:3->1:2)

Sources & evidence

ORD record
ord-8c5be9e4500749b4885c89e0bedfa0d7
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Reaction notes

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