Hydrochloric Acid → 3-(3-Pentylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane fumarate

HRID 260355Notes

Reaction equation

HRID 260355 reaction equation
[C:1](O)(=O)[C:2]([OH:4])=[O:3].Cl[C:8]1[C:12]([CH:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[N:11][S:10][N:9]=1.O.[SH2:22].[Na].[C:24](=[O:27])([O-])[O-:25].[K+].[K+].[CH2:30](Br)[CH2:31][CH2:32][CH2:33][CH3:34].Cl>CN(C=O)C>[C:24]([OH:25])(=[O:27])/[CH:8]=[CH:1]/[C:2]([OH:4])=[O:3].[CH2:30]([S:22][C:8]1[C:12]([CH:13]2[CH:18]3[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]3)[CH2:14]2)=[N:11][S:10][N:9]=1)[CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 217085453-(3-Chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane oxalateHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 217085713-(3-Pentylthio-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane fumarate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)-1-azabicyclo[2.2.2]octane oxalate (500 mg, 1.56 mmol), sodiumhydrogen sulfide, monohydrate (463 mg, 6.25 mmol) and potassium carbonate (1.38 g, 10 mmol) in DMF (20 ml) was stirred at room temperature for 1 h. 1-Pentylbromide (755 mg, 5 mmol) was added, and the reaction mixture was stirred at room temperature for 18 h. 1N HCl was added, and the mixture extracted with ether once. 50% NaOH was added to the aqueous phase and extracted with ether. The ether phase was dried and evaporated. Crystallization of the residue with fumaric acid from isopropanol/ether gave the title compound in 380 mg yield. (Compound 12). M.p. 138°-139° C.

Workup

  1. extractionthe mixture extracted with ether once
  2. addition50% NaOH was added to the aqueous phase
  3. extractionextracted with ether
  4. dry with materialThe ether phase was dried
  5. customevaporated
  6. customCrystallization of the residue with fumaric acid from isopropanol/ether

Sources & evidence

ORD record
ord-43a01166d5cb46dcb5d4fd8da21e3210
Source dataset
uspto-grants-1996_06
Patent number
US05527813

Reaction notes

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