1,2-Diaminocyclohexane, trans- → HCID 49872255, compound

HRID 80143Notes

Reaction equation

HRID 80143 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].[Cl:14][C:15]1[CH:22]=[C:21](I)[CH:20]=[CH:19][C:16]=1[C:17]#[N:18].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[Cl:14][C:15]1[CH:22]=[C:21]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 179660212-Chloro-4-iodobenzonitrileHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 49872255HCID 49872255, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.8465 mmol) was reacted with 2-chloro-4-iodo-benzonitrile (245.3 mg. 0.9311 mmol), 1,4-dioxane (20 mL), copper iodide (16.1 mg, 0.08465 mmol), trans-1,2-diamino cyclohexane (12.6 mg, 0.1100 mmol) and potassium phosphate (30.6 mL, 0.254 mmol) to afford the crude product which was purified by column chromatography on silica gel (2% MeOH in CHCl3). The residue was washed with hexane and dried to afford 85 mg of the product (32% yield).

Workup

  1. customto afford the crude product which
  2. customwas purified by column chromatography on silica gel (2% MeOH in CHCl3)
  3. washThe residue was washed with hexane
  4. customdried

Sources & evidence

ORD record
ord-5c0a1bfcdb1144ee9208b90598c2ec26
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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