Triethylamine → HCID 59588790, compound

HRID 1619240Notes

Reaction equation

HRID 1619240 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](Cl)[S:8][C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH:19]1([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([N:27]3[CH2:28][CH2:29][N:24]([CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[CH2:25][CH2:26]3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8064211-CyclopentylpiperazineHCID 20498716-Bromo-2-chlorobenzothiazole

Product 1

HCID 59588790HCID 59588790, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-bromo-2-chlorobenzothiazole (3 g, 12.1 mmol) in ethanol (50 mL) was added triethylamine (5.04 mL, 36.3 mmol) and 1-cyclopentylpiperazine (1.86 g, 12.1 mmol). The reaction mixture was heated at reflux for 16 h and then concentrated under reduced pressure. The residue was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford 4.3 g (99%) of 6-bromo-2-(4-cyclopentylpiperazin-1-yl)benzothiazole.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f3314f2f10404d6d9f387b0431a1b4c7
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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