Trifluoroacetic acid → HCID 23109887, compound

HRID 1820308Notes

Reaction equation

HRID 1820308 reaction equation
FC(F)(F)C(O)=O.[C:8]1([CH3:30])[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[NH:16][CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1>C(Cl)Cl>[C:10]1([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=[C:8]([CH3:30])[C:9]=1[NH:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57888629HCID 57888629, compound

Product 1

HCID 23109887HCID 23109887, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding trifluoroacetic acid (10 mL) to a solution of tert-butyl 4-(mesitylamino)piperidine-1-carboxylate (5.71 g, 17.9 mmol) in methylene chloride (30 mL), the mixture was stirred at room temperature for 22 hours and then concentrated under reduced pressure. The residue was dissolved in methanol (10 mL), toluene (20 mL) was added, and concentration under reduced pressure was repeated. The residue was purified by silica gel column chromatography (75 g NH silica Chromatorex DM2035, hexane:ethyl acetate=4:1-1:1-chloroform:methanol=10:1) to obtain the title compound as a brown solid (3.57 g) (65% yield, 2 steps).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (10 mL)
  3. additiontoluene (20 mL) was added
  4. concentrationconcentration under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (75 g NH silica Chromatorex DM2035, hexane:ethyl acetate=4:1-1:1-chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e3c0e596a96e404dae1a817b1065b7f7
Source dataset
uspto-grants-2009_10
Patent number
US07601843B2

Reaction notes

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