Water → HCID 67450532, compound

HRID 1465809Notes

Reaction equation

HRID 1465809 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].[CH2:12]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[CH2:12]([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)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 4243221-Butylpiperazine

Product 1

HCID 67450532HCID 67450532, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (4.05 g, 23.5 mmol), 1-n-butyl-piperazine (10.0 g, 70 mmol) and anhydrous potassium carbonate (3.6 g, 26 mmol) in N,N-dimethylacetamide (10 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 into cold water and stirred vigorously for 3 hours. 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, filtered, washed with additional diethyl ether, dried to afford 5-(4-butyl-piperazin-1-yl)-2-nitro-phenylamine (4.4 g, 67%) as a yellow powder, and used in the next step without further purification.

Workup

  1. stirringstirred vigorously for 3 hours
  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-2610e452a0894ca8a7d28551be0bb4c1
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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