Water → 3-(4-Fluoropiperidin-1-yl)-2-nitropyridine

HRID 451516

Reaction equation

HRID 451516 reaction equation
Cl.[F:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.FC(F)(F)S(O[C:22]1[C:23]([N+:28]([O-:30])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=1)(=O)=O.O>CC(N(C)C)=O>[F:2][CH:3]1[CH2:8][CH2:7][N:6]([C:22]2[C:23]([N+:28]([O-:30])=[O:29])=[N:24][CH:25]=[CH:26][CH:27]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27591584-Fluoropiperidine hydrochlorideHCID 108802252-Nitropyridin-3-yl trifluoromethanesulfonate

Product 1

HCID 673355063-(4-Fluoropiperidin-1-yl)-2-nitropyridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-fluoropiperidine hydrochloride (1.54 g, 11 mmol) and triethylamine (4.5 mL, 33 mmol) in dimethylacetamide (30 mL) was added 2-nitropyridin-3-yl trifluoro-methanesulfonate (3.00 g, 11 mmol) and the mixture heated to 110° C. for 1 hour. Water was added and the mixture extracted with ethyl acetate. The organic phase was washed with brine and dried with sodium sulfate. The solvent was evaporated in vacuo and the product used without further purification. The title compound was obtained as a yellow oil (2.22 g, 89%).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried with sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe product used without further purification

Sources & evidence

ORD record
ord-b1fc0a0987334b61ba2a9df044f6e036
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Linked notes

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