Trifluoroacetic acid → 2-[4-(4-Fluorophenoxy)phenyl]ethan-1-amine

HRID 474720Notes

Reaction equation

HRID 474720 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]([F:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl.C([O-])(O)=O.[Na+]>[F: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][NH2:7])=[CH:11][CH:12]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67776301{2-[4-(4-Fluoro-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 209919212-[4-(4-Fluorophenoxy)phenyl]ethan-1-amineYield 100.3%

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-(4-fluoro-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (3.018 mmol, 1 eq) was dissolved in dichloromethane (10 ml) and stirred at 0° C. for 5 min. TFA (15.088 mmol, 5 eq) was added and stirring was continued for overnight. Reaction mixture was diluted with 50 ml NaHCO3 (sat.) and extraction with DCM (3×20 ml) followed. Organic layers were combined and evaporated in vacuo to give 2-[4-(4-fluoro-phenoxy)-phenyl]ethylamine (3.027 mmol, yield=94%, purity=94%). [M+H]+=265.25 1H NMR (300 MHz, CDCl3) δ/ppm 2.86 (s, 2H), 3.09 (s, 2H), 7.01 (d, J=8.7 Hz, 5H), 7.24 (s, 2H), 7.37 (s, 1H)

Workup

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

Sources & evidence

ORD record
ord-acce05acdd0c424f9b6da56902bd9343
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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