Trifluoroacetic acid → 4-(4-chlorophenoxy)Benzeneethanamine

HRID 705960Notes

Reaction equation

HRID 705960 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]([Cl:23])=[CH:19][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][NH2:7])=[CH:11][CH:12]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67772786{2-[4-(4-Chloro-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 231324504-(4-chlorophenoxy)BenzeneethanamineYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{2-[4-(4-Chloro-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (600 mg, 1.72 mmol, 1 eq) and TFA (658 μl) were dissolved in 50 ml of dry DCM under argon atmosphere. The mixture was stirred at room temperature for 60 hours. The solvent was evaporated, the resulting crude was dissolved in 10 ml of MeOH and was purified using 20 g SCX column. The free base was rinsed from the column using 1 N NH3/ethanol solution. The solvent was evaporated and obtained was 2-[4-(4-chloro-phenoxy)-phenyl]-ethylamine (404 mg, yield=90.8%, purity=96%) in form of yellowish oil. MS: [M+H]+=248.21 1H NMR (300 MHz; CDCl3) δ/ppm 1.22 (s, 2H), 2.71 (t, J=6.62 Hz, 2H), 2.95 (t, J=6.62 Hz, 2H), 6.85-6.96 (m, 4H), 7.16 (d, J=7.60 Hz, 2H), 7.25 (d, J=7.60 Hz, 2H)

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe resulting crude was dissolved in 10 ml of MeOH
  3. customwas purified
  4. washThe free base was rinsed from the column
  5. customThe solvent was evaporated
  6. customobtained

Sources & evidence

ORD record
ord-5949f5f117564e069715de9a1df48eb6
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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