Hydrochloric Acid → 2-(4-Fluoro-piperidinyl)-4-amino-5-nitro-benzoic acid

HRID 1189637Notes

Reaction equation

HRID 1189637 reaction equation
[F:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Cl.F[C:10]1[CH:18]=[C:17]([NH2:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>CN(C=O)C>[F:1][CH:2]1[CH2:7][CH2:6][N:5]([C:10]2[CH:18]=[C:17]([NH2:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27591594-FluoropiperidineHCID 597853374-Amino-2-fluoro-5-nitrobenzoic acid

Product 1

HCID 679575752-(4-Fluoro-piperidinyl)-4-amino-5-nitro-benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-fluoropiperidine×HCl (691 mg, 4.9 mmol), TEA (2.2 ml, 16 mmol), 2-fluoro-4-amino-5-nitro-benzoic acid (900 mg, 4.5 mmol) and DMF (15 mL) is stirred for 4.5 h at 50° C. Then the mixture is concentrated, diluted with water and the precipitate is filtered and dried.

Workup

  1. concentrationThen the mixture is concentrated
  2. additiondiluted with water
  3. filtrationthe precipitate is filtered
  4. customdried

Sources & evidence

ORD record
ord-35ee84f79cc6462dbbf0a5b683efb792
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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