Piperidine → Benzoic acid, 3-nitro-4-(1-piperidinyl)-, methyl ester

HRID 406391Notes

Reaction equation

HRID 406391 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19]>CN(C=O)C.C(OCC)(=O)C>[N+:18]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:12]([O:14][CH3:15])=[O:13])([O-:20])=[O:19]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 2878938Benzoic acid, 3-nitro-4-(1-piperidinyl)-, methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Piperidine (1.24 ml) was added to a solution of methyl 4-fluoro-3-nitrobenzoate (1.00 g) in DMF (20 ml) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, sequentially washed with water and brine, and dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.50 g).

Workup

  1. washsequentially washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f75e44dcf4314daaae7c41e3b371dbdc
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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