Triethylamine → 9-(4-Bromobutyl)-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxamide

HRID 2415844Notes

Reaction equation

HRID 2415844 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1([C:19](Cl)=[O:20])[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2.Cl.[F:23][C:24]([F:28])([F:27])[CH2:25][NH2:26].C(N(CC)CC)C>ClCCl>[F:23][C:24]([F:28])([F:27])[CH2:25][NH:26][C:19]([C:6]1([CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 105227589-(4-bromo-butyl)-9H-fluorene-9-carboxylic Acid Chloride

Product 1

HCID 105264379-(4-Bromobutyl)-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

23 g (0.063 mol) of 9-(4-bromo-butyl)-9H-fluorene-9-carboxylic acid chloride are added dropwise to a solution of 9.35 g (0.069 mol) of 2,2,2-trifluoroethylamine-hydrochloride and 26 ml (0.188 mol) of triethylamine in 550 ml of dichloromethane at 0° C. under nitrogen and stirred for 2 hours at ambient temperature. The reaction mixture is extracted twice each with water, 1N hydrochloric acid and sodium hydrogen carbonate solution. The organic phase is dried over sodium sulphate and the solvent is distilled off. The product is purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=8:1).

Workup

  1. extractionThe reaction mixture is extracted twice each with water, 1N hydrochloric acid and sodium hydrogen carbonate solution
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. distillationthe solvent is distilled off
  4. customThe product is purified by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate=8:1)

Sources & evidence

ORD record
ord-a846cff74c5f48f4b25c526a09408517
Source dataset
uspto-grants-2004_11
Patent number
US06821967B2

Reaction notes

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