Trifluoroacetic acid → (R)-2-((2-cyano-3-nitrophenoxy)methyl)piperidin-1-ium 2,2,2-trifluoroacetate

HRID 1483959Notes

Reaction equation

HRID 1483959 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[C:17]=1[C:25]#[N:26])=O)(C)(C)C.[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>C(Cl)Cl>[F:27][C:28]([F:33])([F:32])[C:29]([O-:31])=[O:30].[C:25]([C:17]1[C:18]([N+:22]([O-:24])=[O:23])=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH2:14][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][NH2+:8]1)#[N:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86714287(R)-tert-butyl-2-((2-cyano-3-nitrophenoxy)methyl)piperidine-1-carboxylate

Product 1

HCID 86714290(R)-2-((2-cyano-3-nitrophenoxy)methyl)piperidin-1-ium 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 2-((2-cyano-3-nitrophenoxy)methyl)piperidine-1-carboxylate (Example 15e, 2.18 g, 6.03 mmol) in anhydrous DCM (65 mL) was added trifluoroacetic acid (7.91 mL) at room temperature. The reaction mixture was stirred at room temperature for over 1 hour. The solvent was removed under reduced pressure and the residue was dried under the vacuum to give the title product which could be used for the next step reaction without further purification. MS 262 (MH+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was dried under the vacuum

Sources & evidence

ORD record
ord-6e607124d578491d8af363dbb2068f9f
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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