Triethylamine → 3-(((4-Phenylbutyl)amino)carbonyl)aniline hydrochloride

HRID 609564Notes

Reaction equation

HRID 609564 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[N+:19]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([Cl:27])=[O:26])([O-])=O.C(O)(C)C.Cl>C1COCC1.CO.[Pd]>[ClH:27].[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:25]([C:24]2[CH:23]=[C:22]([CH:30]=[CH:29][CH:28]=2)[NH2:19])=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 83242BenzenebutanamineHCID 21912024Isopropanol hydrochloride

Product 1

HCID 193536943-(((4-Phenylbutyl)amino)carbonyl)aniline hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-phenylbutylamine, 2.9 g, 0.019 moles, in 100 ml THF was added 10 ml of triethylamine. To this was added 3-nitrobenzoyl chloride, 3.0 g, 0.016 moles and the reaction was stirred at room temperature for 18 hours. The triethylamine hydrochloride was removed by filtration. To the filtrate was added 100 ml of ethyl acetate, and the organic phase was then washed with 1N hydrochloric acid, 100 ml (twice), and then with 2N sodium hydroxide, 100 ml (twice). The organic phase was dried over magnesium sulfate. The solvent was evaporated to yield an oil. This oil was dissolved in 100 ml of methanol and 20 ml of isopropanol/hydrochloric acid and to this solution was added 250 mg of 10% palladium on carbon. The reaction was hydrogenated for 3 hours. The catalyst was removed by filtration and the solvent was evaporated. The residue was crystallized from hot isopropanol and ethyl acetate, and was collected by filtration to yield 3.1 g of 3-(((4-phenylbutyl)amino)carbonyl)aniline hydrochloride.

Workup

  1. customThe triethylamine hydrochloride was removed by filtration
  2. additionTo the filtrate was added 100 ml of ethyl acetate
  3. washthe organic phase was then washed with 1N hydrochloric acid, 100 ml (twice), and then with 2N sodium hydroxide, 100 ml (twice)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customto yield an oil
  7. waitThe reaction was hydrogenated for 3 hours
  8. customThe catalyst was removed by filtration
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from hot isopropanol and ethyl acetate
  11. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-649f81769c52498f95df79ff891248f3
Source dataset
uspto-grants-1999_12
Patent number
US05998399

Reaction notes

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