1,2-Diaminocyclohexane, trans- → HCID 53255666, compound

HRID 2245004Notes

Reaction equation

HRID 2245004 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][C:10]1=[O:15].[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>O1CCOCC1.[Cu]I>[N:9]1([CH:3]2[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]2)[CH2:14][CH2:13][O:12][CH2:11][C:10]1=[O:15]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 669533-MorpholinoneHCID 881004-Bromopyridinium chloride

Product 1

HCID 53255666HCID 53255666, compoundYield 11.5%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

A mixture of 4-bromopyridine hydrochloride (778 mg, 4.00 mmol), 3-morpholinone (404 mg, 4.00 mmol), K3PO4 (1.70 g, 8.00 mmol) and 1,2-trans-diaminocyclohexane (200 uL, 1.60 mmol) in dioxane (10 mL) was degassed with Ar before being charged with CuI (152 mg, 0.80 mmol). The mixture in a sealed tube was heated at 110° C. overnight. The mixture was applied to a silica gel column, which was then eluted with 2-5% MeOH in CH2Cl2 to give the desired product (85 mg). MS 179.5 (M+H).

Workup

  1. customwas degassed with Ar
  2. washwas then eluted with 2-5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-416168f462a14ca799c083538367f1c7
Source dataset
uspto-grants-2010_03
Patent number
US07678913B2

Reaction notes

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