Trifluoroacetic acid → 2-Methyl-N-[4-methyl-3-(4-piperidinyl)phenyl]propanamide

HRID 1269141Notes

Reaction equation

HRID 1269141 reaction equation
[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[CH:12]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:3][CH:2]([CH3:4])[C:1]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:26])=[C:11]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16756289Tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]1-piperidinecarboxylate

Product 1

HCID 167572542-Methyl-N-[4-methyl-3-(4-piperidinyl)phenyl]propanamideYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-1-piperidinecarboxylate (335 mg, 0.930 mmol) in CH2Cl2 (10.0 mL) was added TFA (10.0 mL) at room temperature. The reaction mixture was stirred for 2 h and concentrated in vacuo. The residue was dissolved in 20 mL of CHCl3/i-PrOH (3:1) and was basified with 5% KOH solution (10 mL). The aqueous layer was extracted with CHCl3/i-PrOH (3:1, 3×10 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give 2-methyl-N-[4-methyl-3-(4-piperidinyl)phenyl]propanamide (190 mg, 78%): ESMS m/e: 261.0 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in 20 mL of CHCl3/i-PrOH (3:1)
  3. extractionThe aqueous layer was extracted with CHCl3/i-PrOH (3:1, 3×10 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-022bc729d34b444cb3f1861ee630fc0b
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

Loading…