Trifluoroacetic acid → Methyl-{2-[4-(3-trifluoromethyl-phenoxy)-phenyl]ethyl}-amine

HRID 705956Notes

Reaction equation

HRID 705956 reaction equation
C(O[C:6](=O)[N:7](C)[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>[CH3:6][NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:26])[F:25])[CH:18]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67774263Methyl-{2-[4-(3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 67775155Methyl-{2-[4-(3-trifluoromethyl-phenoxy)-phenyl]ethyl}-amineYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl-{2-[4-(3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (300 mg, 0.759 mmol, 1 eq) was dissolved in dry DCM (3 ml) under argon atmosphere and TFA (290.6 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 product methyl-{2-[4-(3-trifluoromethyl-phenoxy)-phenyl]-ethyl}-amine (211.5 mg, yield=82.1%, purity=87%). [M+H]+=296.31 1H NMR (300 MHz; CDCl3) δ/ppm 2.44 (s, 3H), 2.74-2.89 (m, 4H), 6.90-6.98 (m, 2H), 7.09-7.22 (m, 4H), 7.27-7.33 (m, 1H), 7.35-7.45 (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-fd11b2511e244defbdbbd3797d62c81b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…