Dimethylformamide → HCID 22458095, compound

HRID 1420572Notes

Reaction equation

HRID 1420572 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-40087127868b41b2adcadfaf8c197846
Source dataset
uspto-grants-2000_06
Patent number
US06071920

Reaction notes

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