Trifluoroacetic acid → HCID 86721019, compound

HRID 524962Notes

Reaction equation

HRID 524962 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:21]C(=O)OC(C)(C)C)[CH2:11][C:10]1=[O:29].CO.C(Cl)Cl>C(Cl)Cl>[NH2:21][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[CH:12]1[CH2:13][CH2:14][N:9]([CH3:8])[C:10](=[O:29])[CH2:11]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 86721017HCID 86721017, compound

Product 1

HCID 86721019HCID 86721019, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.75 mL, 9.735 mmol) was added to a solution of tert-butyl N-[4-(1-methyl-2-oxo-4-piperidyl)-3-pyridyl]carbamate (74 mg, 0.2423 mmol) in DCM (2 mL) and was stirred at ambient temperature for 2 hours. The reaction mixture was adsorbed onto a pre-wetted (methanol/DCM (1:1), 2 mL) SCX-2 cartridge (2 g) and flushed with DCM/methanol (1:1, 20 mL) and then the basic components eluted with 2 M ammonia in methanol (20 mL). The basic eluent was evaporated to dryness to afford 4-(3-aminopyridin-4-yl)-1-methylpiperidin-2-one as a pale yellow oil (50 mg, 97%). MS (ES+) 206.1.

Workup

  1. customflushed with DCM/methanol (1:1, 20 mL)
  2. washthe basic components eluted with 2 M ammonia in methanol (20 mL)
  3. customThe basic eluent was evaporated to dryness

Sources & evidence

ORD record
ord-f0b3bd14248b49ffa26c370103064a8f
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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