p-Fluoronitrobenzene → 4-(Piperidin-1-ylmethyl)aniline

HRID 2236422Notes

Reaction equation

HRID 2236422 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH2:17][CH2:16]N[CH2:14][CH2:13]1.[C:18]([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[N:12]1([CH2:11][C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=2)[CH2:17][CH2:16][CH2:18][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 531671-Methylpiperazine

Product 1

HCID 8461504-(Piperidin-1-ylmethyl)anilineYield 111.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Fluoro-4-nitro-benzene (1.00 g, 7.09 mmol) is dissolved in N,N-dimethylformamide (20 mL), and to this solution, is added 1-methyl-piperazine (0.944 mL, 8.51 mmol) followed by K2CO3 (1.47 g, 10.6 mmol). After stirring the mixture at room temperature for 18 h, the solvent is removed via high vacuum. The resulting residue is dissolved in EtOAc (100 mL) and washed with H2O (10 mL) and brine (10 mL) and then dried (Na2SO4). The solvent is taken off via high vacuum to afford the product as a solid (1.50 g, 96%); 1H NMR (DMSO-d6) δ 2.17 (s, 3H), 2.37-2.42 (m, 4H), 3.39-3.43 (m, 4H), 6.98 (d, J=9.6 Hz, 2H), 8.00 (d, J=9.5 Hz, 2H); mass spectrum [(+) ESI], m/z 222 (M+H)+.

Workup

  1. customthe solvent is removed via high vacuum
  2. dissolutionThe resulting residue is dissolved in EtOAc (100 mL)
  3. washwashed with H2O (10 mL) and brine (10 mL)
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-d946130bd54f452abe6d1d870439fdb1
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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