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

HRID 705972Notes

Reaction equation

HRID 705972 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][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([Cl:27])[CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl.C([O-])(O)=O.[Na+]>[Cl:27][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=1[C:23]([F:24])([F:25])[F:26])[O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][NH2:7])=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67774227{2-[4-(3-Chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 677754622-[4-(3-Chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamineYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Entire reaction was performed under argon atmosphere using syringe septa technique. {2-[4-(3-chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (3.703 mmol, 1 eq) was dissolved in dichloromethane (20 ml) and stirred at 0° C. for 5 min. TFA (18.517 mmol, 5 eq) was added and stirring was continued overnight. Reaction mixture was diluted with 10 ml NaHCO3 (sat.) and extraction with DCM (3×20 ml) followed. Organic layers were combined and evaporated in vacuo to give 2-[4-(3-chloro-4-trifluoromethyl-phenoxy)-phenyl]-ethylamine (2.661 mmol, yield=72%, purity=99%). [M+H]+=316.21 1H NMR (300 MHz, CDCl3) δ/ppm 2.68-2.82 (m, 2H), 2.91-3.05 (m, 2H), 6.81-6.91 (m, 1H), 6.93-7.07 (m, 4H), 7.16-7.23 (m, 1H), 7.52-7.63 (m, 1H)

Workup

  1. customEntire reaction
  2. stirringstirring
  3. waitwas continued overnight
  4. customReaction mixture
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-52f29530a6624db5a81e7f2e8c252686
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…