Water → HCID 67450488, compound

HRID 1465807Notes

Reaction equation

HRID 1465807 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].[CH:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH:12]([N:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:7])[CH:8]=2)[CH2:17][CH2:16]1)([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 780131-Isopropylpiperazine

Product 1

HCID 67450488HCID 67450488, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (1.35 g, 7.8 mmol), 1-isopropyl-piperazine (2.0 g, 15.6 mmol) and anhydrous potassium carbonate (1.18 g, 8.6 mmol) in N,N-dimethylacetamide (2.5 ml) was stirred at 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 onto cold water and stirred vigorously for 3 h. The resulting brown precipitate was collected by filtration, washed well with water then dried on the filter funnel. The resulting brown solid was slurried in diethyl ether, filtered, washed with additional diethyl ether, dried to afford 5-(4-Isopropyl-piperazin-1-yl)-2-nitro-phenylamine (1.1 g, 53%) and used in the next step without further purification.

Workup

  1. stirringstirred vigorously for 3 h
  2. filtrationThe resulting 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-a6697953157649c5ae495a8da575be68
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

Loading…