Trifluoroacetic acid → HCID 67774711, compound

HRID 474726Notes

Reaction equation

HRID 474726 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][C:13]2[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][NH:7][CH3:6])=[CH:11][CH:12]=2)=[CH:18][C:19]=1[C:24]([F:25])([F:26])[F:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67774886{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 67774711HCID 67774711, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

{2-[4-(4-Chloro-3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.08 g, 2.51 mmol, 1 eq) was dissolved in dry DCM (10 ml) under argon atmosphere and TFA (961 μl, 5 eq) was added. Reaction mixture was stirred for overnight. In the reaction mixture was added more DCM (15 ml) and was extracted with saturated NaHCO3 (3×15 ml) and brine. Organic layer was dried over anhydrous Na2SO4, filtered and evaporated to give a crude product. Crude product was purified via Biotage SP-1 Snap Si 25 g; 25 ml/min; UV Wavelength (Collection: 254 nm; Monitor: 290 nm) in the gradient of MeOH in DCM: 2% for 1.5 CV, 2-10% for 20 CV. The appropriate fractions were combined and product 2-[4-(3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (501 mg, yield=58.1%, purity 96%). [M+H]+=330.75 1H NMR (300 MHz; CDCl3) δ/ppm 2.47 (s, 3H), 2.78-2.92 (m, 4H), 6.91-7.10 (m, 3H), 7.19-7.33 (m, 3H), 7.41 (d, J=8.99 Hz, 1H)

Workup

  1. customReaction mixture
  2. extractionwas extracted with saturated NaHCO3 (3×15 ml) and brine
  3. dry with materialOrganic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f69a6a1422d943cf848c44ebbbf3e235
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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