Piperazine → N-(1-(3,5-dichlorophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzeneamine

HRID 1910638Notes

Reaction equation

HRID 1910638 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][C:12]2[CH:17]=[C:16](F)[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][C:12]2[CH:17]=[C:16]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[CH:15]=[CH:14][C:13]=2[N+:19]([O-:21])=[O:20])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 81531DiisopropylethylamineHCID 58707340N-(1-(3,5-dichlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamine

Product 1

HCID 58707285N-(1-(3,5-dichlorophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzeneamineYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(1-(3,5-dichlorophenyl)ethyl)-5-fluoro-2-nitrobenzenamine (1.62 mmol), piperazine (8.1 mmol), N,N-diisopropylethylamine (0.58 mmol) were stirred at 60° C. in dry acetonitrile (20 mL) for 3 days. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and the crude compound was purified by silica chromatography using 20% ethyl acetate in hexanes to afford the title compound (19% yield). 1H NMR (400 MHz, CDCl3): δ 9.31 (d, 1H), 7.63 (d, 1H), 7.25 (s, 1H), 7.22 (s, 2H), 6.18 (d, 1H), 5.53 (s, 1H), 4.48 (m, 1H), 3.48 (m, 4H), 3.25 (m, 4H), 1.60 (d, 3H), 1.47 (s, 9H); MS (ESI) m/z: Calculated for C18H20O2N4O2: 395.28; Observed: 396.3 (M++1).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. customthe crude compound was purified by silica chromatography

Sources & evidence

ORD record
ord-db4a04a4b5254147817baa205185cd7e
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

Loading…