Dimethylformamide → HCID 22458095, compound

HRID 2184831Notes

Reaction equation

HRID 2184831 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].[NH:14]1[C:22]2[C:17](=[C:18]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1.C(N(CC)CC)C.CN(C=O)C>O>[N+:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[NH:4][CH2:3][CH2:2][N:26]1[CH2:27][CH2:28][N:23]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:17]=2[CH:16]=[CH:15][NH:14]3)[CH2:24][CH2:25]1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 12257331HCID 12257331, compound

Product 1

HCID 22458095HCID 22458095, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 0.49 g of N-(2-chloroethyl)-2-nitroaniline, prepared according to the procedure described by Ramage G. R. et al. in J. Chem. Soc. 4406-4409 (1952), 0.55 g of 1-(4-indolyl)piperazine (prepared according to WO 95/33743), 1 mL of triethylamine and 3 mL of DMF was heated at reflux while stirring under nitrogen for 2.5 h. After cooling at room temperature, the mixture was poured into H2O, extracted with CH2Cl2, and the organic phase dried on anhydrous Na2SO4 and evaporated to dryness. The residue was purified via flash chromatography (EtOAc-petrolium ether 3:7) giving 0.35 g (40%) of the title compound.

Workup

  1. customprepared
  2. temperatureat reflux
  3. extractionextracted with CH2Cl2
  4. dry with materialthe organic phase dried on anhydrous Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified via flash chromatography (EtOAc-petrolium ether 3:7)

Sources & evidence

ORD record
ord-86d14daccb9b46e8ae0b4ecfbc36aeb6
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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