Hydrochloric Acid → 3-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-aza-bicyclo[3.2.1]octane

HRID 40697

Reaction equation

HRID 40697 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][CH:11]([C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)=[CH:18][CH:17]=1)[CH2:12]2)=O)(C)(C)C.Cl.O1CCOCC1>ClCCl>[CH3:31][S:28]([N:25]1[CH2:24][CH2:23][N:22]([C:19]2[CH:18]=[CH:17][C:16]([CH:11]3[CH2:10][CH:9]4[NH:8][CH:13]([CH2:14][CH2:15]4)[CH2:12]3)=[CH:21][CH:20]=2)[CH2:27][CH2:26]1)(=[O:29])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 674120823-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Product 1

HCID 674123703-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-aza-bicyclo[3.2.1]octaneYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[4-(4-Methanesulfonylpiperazin-1-yl)phenyl]-8-azabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.758 g, 1.69 mmol) is solubilized in 158 ml of dichloromethane. 4N HCl in dioxane (4.2 ml, 16.8 mmol) is then added. After stirring for 16 h at ambient temperature, the reaction medium is concentrated, taken up with water, and washed with ethyl acetate. The pH of the aqueous phase is then adjusted to 10 with a 5N aqueous solution of sodium hydroxide. After extraction with dichloromethane, and washing with water and then with a saturated aqueous sodium chloride solution, the organic phase is dried over MgSO4 and then concentrated to dryness. 0.51 g of expected 3-[4-(4-methanesulfonylpiperazin-1-yl)phenyl]-8-aza-bicyclo[3.2.1]octane is obtained, which is subsequently used as it is.

Workup

  1. concentrationthe reaction medium is concentrated
  2. washwashed with ethyl acetate
  3. extractionAfter extraction with dichloromethane
  4. washwashing with water
  5. dry with materialwith a saturated aqueous sodium chloride solution, the organic phase is dried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-479e70835b7d462194d5dd9b232e2334
Source dataset
uspto-grants-2013_09
Patent number
US08530477B2

Linked notes

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