Trifluoroacetic acid → HCID 86666625, compound

HRID 587841Notes

Reaction equation

HRID 587841 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]([CH3:19])[C:4]=1[NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([CH:29]([NH:31]C(=O)OC(C)(C)C)[CH3:30])=[CH:25][CH:24]=1)=[O:22])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:31][CH:29]([C:26]1[CH:25]=[CH:24][C:23]([C:21]([NH:20][C:4]2[C:5]([CH3:19])=[CH:6][C:7]([C:9]([F:18])([C:10]([F:11])([F:12])[F:13])[C:14]([F:15])([F:16])[F:17])=[CH:8][C:3]=2[CH2:1][CH3:2])=[O:22])=[CH:28][CH:27]=1)[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86666626HCID 86666626, compound

Product 1

HCID 86666625HCID 86666625, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-Butyl [1-(4-{[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]carbamoyl}phenyl)ethyl]carbamate (1.7 g) was dissolved in methylene chloride (20 ml). To the solution, trifluoroacetic acid (1.5 g) was added and the mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure and the residue was neutralized by adding water and potassium carbonate followed by extraction twice with ethyl acetate. The organic phases were combined, washed with a saturated sodium bicarbonate aqueous solution and water in turns and dried over anhydrous magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain 4-(1-aminoethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]benzamide as a crude product (1.8 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionby adding water and potassium carbonate
  3. extractionfollowed by extraction twice with ethyl acetate
  4. washwashed with a saturated sodium bicarbonate aqueous solution and water in turns
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering off the drying agent
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1c7c9173073c43fd9e6635af8459e9d8
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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