Trifluoroacetic acid → 2-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamine

HRID 474743Notes

Reaction equation

HRID 474743 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])=[CH:19][N:18]=2)=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl.C([O-])(O)=O.[Na+]>[F:25][C:23]([F:24])([F:26])[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)=[N:18][CH:19]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67775606{2-[4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 167707892-(4-(5-Trifluoromethyl-2-pyridinyloxy)phenyl)ethylamineYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

{2-[4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (2200 mg, 1.135 mmol, 1 eq) was dissolved in dichloromethane (4 ml) and stirred at 0° C. for 5 min. TFA (3084 ml, 40.273 mmol, 7 eq) was added and stirring was continued at rt overnight. Reaction mixture was diluted with NaHCO3 (sat.) and extracted with DCM (3×). Organic layers were combined and evaporated to give 2-[4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethylamine as white solid (1.6 g, yield=99%, purity 99%). [M+H]+=283.26 1H NMR (DMSO-d6, 300 MHz): 2.83-2.91 (m, 2H), 3.03-3.13 (m, 2H), 7.13-7.19 (d, 2H), 7.20-7.24 (d, 1H), 7.30-7.36 (d, 2H), 7.86 (bs, 2H), 8.19-8.25 (m, 1H), 8.53 (s, 1H)

Workup

  1. stirringstirring
  2. waitwas continued at rt overnight
  3. customReaction mixture
  4. extractionextracted with DCM (3×)
  5. customevaporated

Sources & evidence

ORD record
ord-1c6c952ebb0c42c28780c4bab2ded1d6
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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