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

HRID 332969Notes

Reaction equation

HRID 332969 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-80a5303276f44f1d975b73aed8983206
Source dataset
uspto-grants-2014_11
Patent number
US08877922B2

Reaction notes

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