Dimethyl Sulfoxide → HCID 86744770, compound

HRID 2050894Notes

Reaction equation

HRID 2050894 reaction equation
CS(C)=O.C(Cl)(=O)C([Cl:8])=O.O[CH2:12][C:13]12[CH2:20][CH2:19][N:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2.Cl.[CH3:22][O:23][NH2:24]>C(Cl)Cl.CO.C(N(CC)CC)C>[ClH:8].[CH3:22][O:23][N:24]=[CH:12][C:13]12[CH2:20][CH2:19][N:16]([CH2:17][CH2:18]1)[CH2:15][CH2:14]2

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 1413111-Azabicyclo(2.2.2)octane-4-methanolHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 86744770HCID 86744770, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-60 °C

Procedure

1.6 cm3 of dimethyl sulfoxyde are added dropwise to a mixture, cooled to -50°/-60° C., of 1.09 cm3 of oxalyl chloride and 30 cm3 of methylene chloride, after agitating for 15 minutes, 1.6 g of 4-hydroxy methylquinuclidine (Helv. Chim. Acta 57 (8) 2332 (1974)) in 50 cm3 of methylene chloride are added and the medium is agitated for 2 hours at -50°/-60° C. Then, 7.89 cm3 of triethylamine are added dropwise. The mixture is allowed to warm at room temperature, a solution of 0.95 g of O-methyl hydroxylamine hydrochloride in 30 cm3 of methanol is added and the reaction medium is maintained for 16 hours to room temperature. The solvents are evaporated to dryness, the residue is taken up with dichloromethane, alkalized with 2N sodium hydroxyde, after decantation the aqueous phase is then extracted with dichloromethane. The organic extracts are evaporated to dryness. The residue is dissolved in ethyl ether and the hydrochloride is obtained using gaseous hydrochloric acid. The solid is filtered off and crystallised in a mixture of ethanolethyl ether. 0.91 g of expected product is obtained. M.P.=271°-271.5° C. (with decomposition).

Workup

  1. temperatureto warm at room temperature
  2. temperaturethe reaction medium is maintained for 16 hours to room temperature
  3. customThe solvents are evaporated to dryness
  4. extractionafter decantation the aqueous phase is then extracted with dichloromethane
  5. customThe organic extracts are evaporated to dryness
  6. dissolutionThe residue is dissolved in ethyl ether

Sources & evidence

ORD record
ord-a2fc843d51374b61ab5ad40e611e1fb5
Source dataset
uspto-grants-1991_05
Patent number
US05015655

Reaction notes

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