Triethylamine → 6-Bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole

HRID 1619247Notes

Reaction equation

HRID 1619247 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.CCN(CC)CC.[CH:19]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH2:21][CH2:20]1>CCO>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([N:25]3[CH2:26][CH2:27][N:22]([CH:19]4[CH2:21][CH2:20]4)[CH2:23][CH2:24]3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20498716-Bromo-2-chlorobenzothiazoleHCID 47420041-Cyclopropylpiperazine

Product 1

HCID 595888036-Bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazoleYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-bromo-2-chlorobenzothiazole (8.2 g, 33 mmol) in EtOH (115 mL) was added Et3N (16.7 g, 165 mmol), followed by 1-cyclopropylpiperazine (5 g, 39.6 mmol). The mixture was heated at reflux for 12 h. Then the mixture was evaporated to remove EtOH. Water (120 mL) was added to the residue and the mixture was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated to give a residue, which was purified by column chromatography on silica gel eluting with a mixture of EtOAc/petroleum ether (1:10 with 0.1% NH4OH added) to give 3.46 g (31%) 6-bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. customThen the mixture was evaporated
  4. customto remove EtOH
  5. additionWater (120 mL) was added to the residue
  6. extractionthe mixture was extracted with CH2Cl2 (3×50 mL)
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customto give a residue, which
  11. customwas purified by column chromatography on silica gel eluting with a mixture of EtOAc/petroleum ether (1:10 with 0.1% NH4OH added)

Sources & evidence

ORD record
ord-95b29f0564e64845bc24b4586d38f84e
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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