Trifluoroacetic acid → N-methyl-4-piperazin-1-yl-benzofuran-2-carboxamide

HRID 1471674Notes

Reaction equation

HRID 1471674 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[C:8]=2[CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:8]=2[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68024714tert-Butyl 4-(2-(methylcarbamoyl)benzofuran-4-yl)piperazine-1-carboxylate

Product 1

HCID 57405990N-methyl-4-piperazin-1-yl-benzofuran-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(2-(methylcarbamoyl)benzofuran-4-yl)piperazine-1-carboxylate (5.8 g, 16.1 mmol) was stirred in dichloromethane (50 mL) and trifluoroacetic acid (12.4 mL, 161.4 mmol) at rt for 4 h. The solvent was removed by rotary evaporation. The residue was dissolved in dichloromethane and 20 mL of 7 N NH3 in methanol was added. The mixture was evaporated onto silica gel, which was added to a silica gel column and eluted with 0-10% methanol (7 N NH3) in dichloromethane. The collected fractions were combined and the solvent was removed by rotary evaporation to give the title compound. Yield: 3.66 g, 87%. MS m/z 260.6 [M+H]+.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in dichloromethane
  3. addition20 mL of 7 N NH3 in methanol was added
  4. customThe mixture was evaporated onto silica gel, which
  5. additionwas added to a silica gel column
  6. washeluted with 0-10% methanol (7 N NH3) in dichloromethane
  7. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-16b481d3e1c140b3aafbfe5041a8fa9f
Source dataset
uspto-grants-2015_04
Patent number
US09012457B2

Reaction notes

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