Sodium Bicarbonate → HCID 68468390, compound

HRID 502982Notes

Reaction equation

HRID 502982 reaction equation
CO[C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:23]1([C:29]2([C:34]([NH:36][NH2:37])=O)[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[CH:23]1([C:29]2([C:34]3[N:10]4[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]4=[N:37][N:36]=3)[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68470240HCID 68470240, compoundHCID 178494172HCID 178494172, compound

Product 1

HCID 68468390HCID 68468390, compoundYield 13.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
105 °C

Procedure

(1E)-8-Methoxy-2,3,4,5,6,7-hexahydroazocine (614 mg) and p-toluenesulfonic acid monohydrate (207 mg) were added to a toluene (20 ml) solution of 1-cyclohexylcyclopentanecarbohydrazide (762 mg), followed by stirring at 105° C. for 3 days. The reaction solution and chloroform were added to a saturated aqueous sodium hydrogen carbonate solution and then the organic layer was separated. Furthermore, the organic layer washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=97:3) to obtain 152 mg of 3-(1-cyclohexylcyclopentyl)-5,6,7,8,9,10-hexahydro[1,2,4]triazolo[4,3-a]azocine (pale brown solid).

Workup

  1. customthe organic layer was separated
  2. washFurthermore, the organic layer washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=97:3)

Sources & evidence

ORD record
ord-4eeb8f77278b4b0d87539d4181e2f9cd
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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