1,2-Diaminocyclohexane, trans- → HCID 59636273, compound

HRID 80177Notes

Reaction equation

HRID 80177 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:24])[CH:22]=2)[N:17]([CH3:25])[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH3:25])[CH:16]=[C:15]2[N:10]1[CH2:11][CH2:12][N:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[CH3:1])[C:9]1=[O:13]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-oneHCID 687874273-Bromo-5-chloro-1-methyl-1H-indole

Product 1

HCID 59636273HCID 59636273, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 15, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-114b: 150 mg, 0.8465 mmol) was reacted with 3-bromo-5-chloro-1-methyl-1H-indole (I-137a: 226.2 mg, 0.9311 mmol), 1,4-dioxane (20 mL), copper iodide (16.1 mg, 0.8465 mmol), trans-1,2-diamino cyclohexane (30.6 mL, 0.255 mmol) and potassium phosphate (441 mg, 2.077 mmol). The resulting mixture was heated to reflux for 16 hours. The reaction workup afforded 170 mg of 1-(5-Chloro-1-methyl-1H-indol-3-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (58.9% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 16 hours

Sources & evidence

ORD record
ord-f4c196404b824480b0c8bb525fdabe7c
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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