Trifluoroacetic acid → N-(4-Nitro-3-(trifluoromethyl)phenyl)piperidin-4-amine

HRID 1772192Notes

Reaction equation

HRID 1772192 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[CH:6][C:5]=1[C:24]([F:27])([F:26])[F:25])([O-:3])=[O:2].FC(F)(F)C(O)=O>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)=[CH:6][C:5]=1[C:24]([F:27])([F:25])[F:26])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58577140Tert-butyl 4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]piperidine-1-carboxylate

Product 1

HCID 43448257N-(4-Nitro-3-(trifluoromethyl)phenyl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[[4-nitro-3-(trifluoromethyl)phenyl]amino]piperidine-1-carboxylate (1 g, 2.6 mmol) in dichloromethane (10 mL) was added trifluoroacetic acid (3 ml). The solution was stirred for 2 hours at room temperature and then concentrated under vacuum. The crude material was diluted with water (50 ml), adjusted pH to 9 with sodium bicarbonate (saturated aqueous), and extracted with dichloromethane (3×100 ml). The organic layers were combined and dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to afford N-[4-nitro-3-(trifluoromethyl)phenyl]piperidin-4-amine as a yellow powder (800 mg, crude); (ES, m/z): [M+H]+ 290.1; 1H NMR (300 MHz, DMSO-d6): δ 8.08 (d, J=9.0 Hz, 1H), 7.20-7.80 (br s), 7.60 (d, J=7.8 Hz, 1H), 7.11 (d, J=2.4 Hz, 1H), 6.91 (dd, J=2.4, 9.0 Hz, 1H), 3.70 (m, 1H), 3.22 (d, J=12.6 Hz, 2H), 2.91 (dd, J=10.5, 11.4 Hz, 2H), 1.99 (d, J=11.4 Hz, 2H), 1.52 (m, 2H).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe crude material was diluted with water (50 ml)
  3. extractionextracted with dichloromethane (3×100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ffd7b344d2e042f2a53fdd0401ceaa26
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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