Piperazine → 6-Bromo-2-piperazin-1-yl-1,3-benzothiazole

HRID 447169

Reaction equation

HRID 447169 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[Br:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[S:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 516892Sodium BicarbonateHCID 20498716-Bromo-2-chlorobenzothiazole

Product 1

HCID 422816756-Bromo-2-piperazin-1-yl-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Chloro-6-bromobenzothiazole (2.29 g), piperazine (1.59 g) and sodium bicarbonate (3.10 g) were combined in isopropanol (75 mL) and the resulting orange solution was heated to reflux overnight, then concentrated to ˜15 mL, diluted with water, and extracted with DCM. The extracts were concentrated to yield an orange solid which was chromatographed (0 to 5% MeOH in DCM) to yield 6-bromo-2-(piperazin-1-yl)benzo[d]thiazole as a slightly pink solid. MS: 297.9 (M+H).

Workup

  1. temperaturethe resulting orange solution was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated to ˜15 mL
  4. additiondiluted with water
  5. extractionextracted with DCM
  6. concentrationThe extracts were concentrated
  7. customto yield an orange solid which
  8. customwas chromatographed (0 to 5% MeOH in DCM)

Sources & evidence

ORD record
ord-05bc984d4429494597eea9b37cc37540
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Linked notes

Loading…