1,2-Diaminocyclohexane, trans- → HCID 59840174, compound

HRID 1436517Notes

Reaction equation

HRID 1436517 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](I)=[CH:21][CH:20]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][NH:36][C:35](=[O:39])[CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>[Cu](I)I>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][N:36]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[C:35](=[O:39])[CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 696764-IodoanisoleHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 59840174HCID 59840174, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Conditions

Temperature
100 °C

Procedure

Charge in a pressure tube copper iodide (42 mg, 0.22 mmol), potassium phosphate (1.6 g, 7.5 mmol), trans-1,2-diaminocyclohexane (0.053 ml, 0.44 mmol), p-methoxyphenyl iodide (868 mg, 3.7 mmol) and 3-oxo-piperazine-1-carboxylic acid tert-butyl ester (1.05 g, 4.7 mmol). Purge with nitrogen and add 6 ml of dry toluene. Cap the tube and stir at 100° C. overnight. Filter through celite eluting with EtOAc and concentrate. Purify in a silica gel cartridge (20 g) eluting with EtOAc/hexane 1:1 followed by 100% EtOAc to give the title compound as a white solid (1.03 g, 90%).

Workup

  1. customPurge with nitrogen
  2. additionadd 6 ml of dry toluene
  3. customCap the tube
  4. filtrationFilter through celite
  5. washeluting with EtOAc
  6. concentrationconcentrate
  7. customPurify in a silica gel cartridge (20 g)
  8. washeluting with EtOAc/hexane 1:1

Sources & evidence

ORD record
ord-1be5386e8bae417989d8c355112ae048
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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