1,2-Diaminocyclohexane, trans- → HCID 58945816, compound

HRID 2267149Notes

Reaction equation

HRID 2267149 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N.[C:17]1([N:23]2[CH:27]=[C:26](I)[N:25]=[N:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][NH:39][C:38](=O)[CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>O1CCOCC1.[Cu]I.O>[C:17]1([N:23]2[CH:27]=[C:26]([N:39]3[CH2:38][CH2:37][N:36]([C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[CH2:41][CH2:40]3)[N:25]=[N:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 68429494151451-83-1

Product 1

HCID 58945816HCID 58945816, compoundYield 16.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

In a nitrogen atmosphere, 200 mg of tripotassium phosphate, 5 mg of copper(I) iodide and 0.1 ml of trans-1,2-diaminocyclohexane were successively added to a solution of 50 mg of 1-phenyl-4-iodo-1H-[1,2,3]triazole and 80 mg of 4-(tert-butyloxycarbonyl)piperazin-2-one in 2 ml of dioxane and the mixture was stirred for one night at 90° C. After addition of water, the product was extracted with ethyl acetate and the organic layer washed with water and dried over sodium sulfate. A borane methyl sulfide complex (0.1 ml) was added to the residue after evaporation of the solvent in vacuo and the mixture was stirred at room temperature for 1 hour. After addition of pyridine, the residue prepared by evaporation in vacuo was purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=3:1) to give 10 mg of the title compound as a white solid.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washthe organic layer washed with water
  3. dry with materialdried over sodium sulfate
  4. additionA borane methyl sulfide complex (0.1 ml) was added to the residue
  5. customafter evaporation of the solvent in vacuo
  6. stirringthe mixture was stirred at room temperature for 1 hour
  7. additionAfter addition of pyridine
  8. customthe residue prepared by evaporation in vacuo
  9. customwas purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-96651fd9f2074a0ab5f353b7bae541df
Source dataset
uspto-grants-2010_12
Patent number
US07858800B2

Reaction notes

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