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Hydrochloric Acid → 3-[4-(4-Methane-sulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octane

HRID 40705
Notes
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Reaction equation

HRID 40705 reaction equation
C(OC([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([C:16]1[CH:21]=[C:20]([N:22]3[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]3)[CH:19]=[CH:18][N:17]=1)[CH2:12]2)=O)(C)(C)C.Cl.CO>O1CCOCC1>[CH3:31][S:28]([N:25]1[CH2:26][CH2:27][N:22]([C:20]2[CH:19]=[CH:18][N:17]=[C:16]([N:11]3[CH2:12][CH:13]4[NH:8][CH:9]([CH2:15][CH2:14]4)[CH2:10]3)[CH:21]=2)[CH2:23][CH2:24]1)(=[O:29])=[O:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 674113823-[4-(4-Methanesulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Product 1

HCID 674135353-[4-(4-Methane-sulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octaneYield 101.1%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent
2×

Procedure

3-[4-(4-Methanesulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (0.75 g, 1.66 mmol) is solubilized in 16 ml of dioxane. 4N HCl in dioxane (4.3 ml, 17.5 mmol) is then added, followed by approximately 3 ml of methanol. After stirring for 16 h at ambient temperature, the reaction medium is concentrated, and taken up with water. After extraction with diethyl ether, the pH of the aqueous phase is brought to pH 10 with K2CO3 in the presence of dichloromethane. After extraction with dichloromethane, the organic phase is washed with a saturated aqueous sodium chloride solution, and dried over MgSO4, and then concentrated to dryness. 0.59 g of expected 3-[4-(4-methane-sulfonylpiperazin-1-yl)pyridyl]-3,8-diazabicyclo[3.2.1]octane is obtained, which is subsequently used as it is.

Workup

  1. concentrationthe reaction medium is concentrated
  2. extractionAfter extraction with diethyl ether
  3. extractionAfter extraction with dichloromethane
  4. washthe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2df0e2675781453498a6fb2065307e0d
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530477B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes