2-Fluoroaniline → HCID 51254627, compound

HRID 1246913Notes

Reaction equation

HRID 1246913 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-95a6fd65b7cf4fbd9b19dec21db634fb
Source dataset
uspto-grants-2006_10
Patent number
US07129228B2

Reaction notes

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