1-Bromo-2-Chloroethane → HCID 22458202, compound

HRID 2184848Notes

Reaction equation

HRID 2184848 reaction equation
Br[CH2:2][CH2:3][Cl:4].[NH:5]1[C:13]2[C:8](=[C:9]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1.CCN(C(C)C)C(C)C>O>[Cl:4][CH2:3][CH2:2][N:17]1[CH2:18][CH2:19][N:14]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:8]=2[CH:7]=[CH:6][NH:5]3)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 81531DiisopropylethylamineHCID 5945904-(piperazin-1-yl)-1H-indole

Product 1

HCID 22458202HCID 22458202, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.3 mL of 1-bromo-2-chloroethane, 1.2 g of 1-(4-indolyl)piperazine and 1.2 mL of DIPEA was stirred at 60° C. for 3 h under nitrogen atmosphere. To the solution, cooled at r.t., was added 30 mL of H2O. The mixture was then extracted with CH2Cl2-MeOH 7:3 (3×15 mL). The organic layer, dried on an. Na2SO4, was evaporated to dryness. The crude was purified by flash chromatography (CH2Cl2-MeOH 98:2) to give 0.57 g (36%) of the title compound.

Workup

  1. extractionThe mixture was then extracted with CH2Cl2-MeOH 7:3 (3×15 mL)
  2. customThe organic layer, dried on an
  3. customNa2SO4, was evaporated to dryness
  4. customThe crude was purified by flash chromatography (CH2Cl2-MeOH 98:2)

Sources & evidence

ORD record
ord-3be88735fe204b12b2aecf813acbb9a5
Source dataset
uspto-grants-2002_06
Patent number
US06399614B1

Reaction notes

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