2-Fluoroaniline → HCID 51254627, compound

HRID 479818Notes

Reaction equation

HRID 479818 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=1[NH2:20].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14](=[O:16])[NH:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[F:17])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 10868DicyclohexylcarbodiimideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 51254627HCID 51254627, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 1 (1.0 g, 4.4 mmol), 2-fluoroaniline (463 μl, 4.8 mmol) in CH2Cl2 (25 ml) at 0° C. was added DCC (0.99 g, 4.8 mmol) in several portions. The mixture was stirred at room temperature overnight. The white precipitate was removed by filtration. After removal of solvent, the residue was purified by column chromatography (silica gel, hexane/ethyl acetate, 4:1) to give 3-(2-fluorophenylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester (2) as a colorless oil (1.13 g, 80%).

Workup

  1. customThe white precipitate was removed by filtration
  2. customAfter removal of solvent
  3. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-c86281f1f2ba4e73a7d9dfabcb06da9f
Source dataset
uspto-grants-2003_11
Patent number
US06645980B1

Reaction notes

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