Water → HCID 67449269, compound

HRID 1465822Notes

Reaction equation

HRID 1465822 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH3:12][O:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=2)[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 27346381-(2-Methoxyethyl)piperazine

Product 1

HCID 67449269HCID 67449269, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (1.4 g, 8.1 mmol), 1-(2-methoxy-ethyl)-piperazine (2.0 g, 14.0 mmol) and anhydrous potassium carbonate (1.38 g, 10.0 mmol) in N,N-dimethylacetamide (3 ml) was stirred at 120-130° C. under nitrogen for 1 day. Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water (15 ml) and stirred vigorously. The resulting yellow brown precipitate was collected by filtration, washed well with water then dried on the filter funnel. The resulting yellow brown solid was slurried in diethyl ether (20 mL), filtered, washed with additional diethyl ether, dried to afford 5-[4-(2-methoxy-ethyl)-piperazin-1-yl]-2-nitro-phenylamine (1.7 g, 75%) as a yellow brown powder.

Workup

  1. stirringstirred vigorously
  2. filtrationThe resulting yellow brown precipitate was collected by filtration
  3. washwashed well with water
  4. customthen dried on the filter funnel
  5. filtrationfiltered
  6. washwashed with additional diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-10d87ad5c46a4033932421a58d301bcf
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

Loading…