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

HRID 2280145Notes

Reaction equation

HRID 2280145 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-e358bca296534aec8c4fb9eaafe3cde0
Source dataset
uspto-grants-2015_09
Patent number
US09138013B2

Reaction notes

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