Potassium Iodide → HCID 54236405, compound

HRID 343146Notes

Reaction equation

HRID 343146 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:16][C:17]([N:19]([CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH:28]1([N:19]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C:17](=[O:18])[CH2:16][NH:14][CH:9]2[CH:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:13]=[CH:12][CH:11]=[CH:10]2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68297N-Phenyl-o-phenylenediamineHCID 10638820HCID 10638820, compound

Product 1

HCID 54236405HCID 54236405, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2.03 g (10.7 mmol) N-Phenyl-o-phenylene diamine, 3.50 g (11.2 mmol, 1.05 equiv) 2-Bromo-N-cyclopentyl-N-(4-methoxy-phenyl)-acetamide, prepared as in Part A, 1.62 g (11.7 mmol, 1.1 equiv) Potassium carbonate, and 177 mg (1.1 mmol, 0.1 equiv) Potassium Iodide were combined in 35 mL DMF and stirred 18 h at 60° C. The reaction mixture is filtered and the solvent removed in vacuo. The residue is taken into EtOAc (150 mL), washed with 1N HCl (2×50 mL), H2O (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product is purified by flash chromatography on 50 g silica gel eluted with EtOAc/Hexanes (3:17, 1 L). Appropriate fractions were combined and concentrated in vacuo to give 2.53 g (6.09 mmol) of N-Cyclopentyl-N-(4-methoxy-phenyl)-2-(6-phenylamino-cyclohexa-2,4-dienylamino)-acetamide as a yellow oil: 1H NMR (Acetone-d6, 300 MHz) δ7.26-6.50 (m, 13H), 6.22 (d, 1H, J=7.9), 5.29 (s, br, 1H), 4.82 (m, 1H), 3.87 (s, 3H), 3.41 (d, 2H, J=4.4), 1.83 (m, 2H), 1.48 (m, 4H), 1.33 (m, 2H); TLC Rf =0.14 (EtOAc/Hexanes, 3:17).

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe solvent removed in vacuo
  3. washwashed with 1N HCl (2×50 mL), H2O (50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash chromatography on 50 g silica gel
  8. washeluted with EtOAc/Hexanes (3:17, 1 L)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b174fe767ae465eb0612421d8a771a1
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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