Triethylamine → HCID 11476787, compound

HRID 1025658Notes

Reaction equation

HRID 1025658 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])[C:10]([CH3:16])=[C:11]([C:13](Cl)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.[NH2:25][N:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])[C:10]([CH3:16])=[C:11]([C:13]([NH:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)=[O:14])[N:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166581-AminopiperidineHCID 21949014HCID 21949014, compound

Product 1

HCID 11476787HCID 11476787, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part C: 2-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-1H-imidazole-4-carbonyl chloride (1.5 gram, 3.75 mmol), 1-aminopiperidine (0.725 gram, 7.25 mmol) and triethylamine (0.549 gram, 5.44 mmol) are dissolved in dichloromethane and stirred for one hour at room temperature. The mixture is washed with a saturated aqueous NaHCO3 solution, dried over Na2SO4 and concentrated in vacuo and further purified by column chromatography (heptane/ethyl acetate=1/1 (v/v), silicagel) to give 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide (0.220 gram, 13% yield) as a white foam. MS: 463.

Workup

  1. washThe mixture is washed with a saturated aqueous NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customfurther purified by column chromatography (heptane/ethyl acetate=1/1 (v/v), silicagel)

Sources & evidence

ORD record
ord-2a9941b2f3ed4116a1c80146c4f64402
Source dataset
uspto-grants-2014_05
Patent number
US08729101B2

Reaction notes

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