Trifluoroacetic acid → N-Methyl-N-(piperidin-4-yl)benzamide

HRID 2168193Notes

Reaction equation

HRID 2168193 reaction equation
[CH3:1][N:2]([C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])[CH:3]1[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]([CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[C:16](=[O:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67977238HCID 67977238, compound

Product 1

HCID 12641853N-Methyl-N-(piperidin-4-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-dimethylethyl 4-[methyl(phenylcarbonyl)amino]-1-piperidinecarboxylate D14 (1.66 g) was dissolved in DCM (5 mL) then TFA (4.02 mL, 52.1 mmol) was slowly added. The reaction was stirred at room temperature for 30 minutes. TFA and DCM were removed in vacuo. The crude mixture was poured on a top of an Isolute Si—SCX-2 cartridge, eluting with DCM then MeOH then a 2M NH3 in MeOH solution. Fractions containing desired compound were evaporated in vacuo to give title compound D15 in 1.18 g. LCMS [M+H][email protected] min (2 min run)

Workup

  1. customTFA and DCM were removed in vacuo
  2. additionThe crude mixture was poured on a top of an Isolute Si—SCX-2 cartridge
  3. washeluting with DCM
  4. additionFractions containing desired compound
  5. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-fa1f97b294e3473f8c26d1eaebe79171
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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