1-(3-Fluoro-5-nitrobenzyl)-4-methylpiperazine → 3-Fluoro-5-((4-methylpiperazin-1-yl)methyl)aniline

HRID 1430547Notes

Reaction equation

HRID 1430547 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([N+:16]([O-])=O)[CH:15]=1)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1>CO.[Pd]>[F:1][C:2]1[CH:15]=[C:14]([CH:13]=[C:4]([CH2:5][N:6]2[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]2)[CH:3]=1)[NH2:16]

Participants

4

Reactant 1

HCID 867136821-(3-Fluoro-5-nitrobenzyl)-4-methylpiperazine

Product 1

HCID 867136833-Fluoro-5-((4-methylpiperazin-1-yl)methyl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(3-fluoro-5-nitrobenzyl)-4-methylpiperazine (0.15 g, 0.592 mmol) in MeOH (5 mL) was treated with 10% Pd—C (dry) (0.063 g, 0.059 mmol) and hydrogenated (1 atm) for 3 h. The solids were removed via filtration, rinsed with MeOH and the filtrate concentrated to dryness to afford 3-fluoro-5-((4-methylpiperazin-1-yl)methyl)aniline (100% yield assumed). MS (ESI) m/z: 224.1 [M+H]+.

Workup

  1. customThe solids were removed via filtration
  2. washrinsed with MeOH
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-d62c38f3fadd4e2e8b66b4c960672857
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

Loading…