Trifluoroacetic acid → HCID 62672841, compound

HRID 524865Notes

Reaction equation

HRID 524865 reaction equation
[CH3:1][CH:2]1[N:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][CH:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86720924HCID 86720924, compound

Product 1

HCID 62672841HCID 62672841, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-methyl-4-(3-nitropyridin-4-yl)piperazine-1-carboxylate (prepared according to methods similar to the one depicted in Step 1 of Preparation N-1) in DCM (5 mL) was added TFA (1.445 g, 976.4 μL, 12.67 mmol). The reaction mixture was stirred for 48 h at RT, then the solvent was removed under reduced pressure. The crude was redissolved in MeOH and loaded into a MeOH pre-washed SCX column, rinsed with MeOH and the product was released with methanolic ammonia. The ammonia extracts were concentrated under reduced pressure to yield 2-methyl-1-(3-nitro-4-pyridyl)piperazine (334 mg, 71%). MS (ES+) 223.1.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe crude was redissolved in MeOH
  3. washrinsed with MeOH
  4. concentrationThe ammonia extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-31665f5db7bf4b40ab06d6c30ad5bfe5
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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