Trifluoroacetic acid → 4-[2-(2-Methoxy-phenyl)-ethyl]-pyridin-2-ylamine

HRID 1023448Notes

Reaction equation

HRID 1023448 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH:11]=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][CH2:14][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:7])[CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69085786{4-[2-(2-Methoxy-phenyl)-ethyl]-pyridin-2-yl}-carbamic acid tert-butyl ester

Product 1

HCID 641288554-[2-(2-Methoxy-phenyl)-ethyl]-pyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {4-[2-(2-methoxy-phenyl)-ethyl]-pyridin-2-yl}-carbamic acid tert-butyl ester (143 mg, 0.435 mmol) in dry CH2Cl2 (3 mL) is treated with trifluoroacetic acid (1.0 mL, 13 mmol), and stirred at room temperature. After 18 hours, the reaction mixture is concentrated and the residue is dissolved in CH2Cl2 (10 mL), extracted with saturated aqueous NaHCO3 (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated to give the crude product which is used in the next reaction without purification.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. dissolutionthe residue is dissolved in CH2Cl2 (10 mL)
  3. extractionextracted with saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d5537c7eae8449ab833fe36ee990a14d
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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