Potassium Carbonate → 2-fluoro-4-nitro-N-(2-(piperidin-1-yl)ethyl)aniline

HRID 56187

Reaction equation

HRID 56187 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[F:26]>CC(C)=O>[F:26][C:18]1[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:17]=1[NH:9][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 33944N-(2-Aminoethyl)piperidineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 523235752-fluoro-4-nitro-N-(2-(piperidin-1-yl)ethyl)aniline

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-(piperidin-1-yl)ethanamine (0.90 g, 7.02 mmol) and K2CO3 (0.97 g, 7.02 mmol) in acetone (30 mL) was added 1,2-difluoro-4-nitrobenzene (1.11 g, 6.98 mmol) in one portion in an ice bath and the mixture was refluxed overnight, cooled to rt and filtered. The filtrate was concentrated in vacuo to give the crude product, which was used for next step without further purification.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-21db24e4e1534aff9214e05e442c933c
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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