Trifluoroacetic acid → 2-[4-(3-Trifluoromethyl-phenoxy)-phenyl]-ethylamine

HRID 474717Notes

Reaction equation

HRID 474717 reaction equation
C(OC(=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][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:24][C:23]([F:25])([F:26])[C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][CH2:8][NH2:7])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67772730{2-[4-(3-Trifluoromethyl-phenoxy)-phenyl]ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 677762212-[4-(3-Trifluoromethyl-phenoxy)-phenyl]-ethylamineYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

{2-[4-(3-Trifluoromethyl-phenoxy)-phenyl]ethyl}-carbamic acid tert-butyl ester (354 mg, 0.928 mmol, 1 eq) was dissolved in dry DCM (3 ml) under argon atmosphere and TFA (355 μl, 5 eq) was added. Reaction mixture was stirred for 5 h. 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 product 2-[4-(3-trifluoromethyl-phenoxy)-phenyl]-ethylamine (206 mg, yield=64.7%, purity=65%). [M+H]+=282.28 1H NMR (300 MHz; CDCl3) δ/ppm 2.76-2.80 (m, 2H), 2.93-3.04 (m, 2H), 6.92-6.98 (m, 2H), 7.02-7.35 (m, 5H), 7.37-7.45 (m, 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-e381c9280a5d4312a7767c0021209964
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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