Piperazine → 2-Piperazin-1-yl-1,3-benzothiazole

HRID 1596205Notes

Reaction equation

HRID 1596205 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 119872-Chlorobenzothiazole

Product 1

HCID 5921222-Piperazin-1-yl-1,3-benzothiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-chlorobenzothiazole (5 g) in 20 mL of toluene is added dropwise to a refluxing solution of piperazine (20 g) in 150 mL of toluene. The solution is heated for an additional 24 hours, and after cooling at 0° C. for about 30 minutes, filtered. The filtrate is extracted with 10% acetic acid and the aqueous extracts are washed with ether, basified and extracted with dichloromethane. The dichloromethane layer is washed with water, dried and concentrated. The concentrated material is placed under vacuum overnight (6.8 g, m.p. 63-64° C.). 1H NMR (CDCl3) 7.62 (d, J=8.0 Hz, 1H), 7.55 (d, J=8.0 Hz, 1H), 7.29 (td, J=7.6, 1.2 Hz, 1H), 7.07 (t, J=8.0 Hz, 1H), 3.61 (t, J=5.2 Hz, 4H), 3.00 (t, J=5.2 Hz, 4H).

Workup

  1. temperatureThe solution is heated for an additional 24 hours
  2. filtrationfiltered
  3. extractionThe filtrate is extracted with 10% acetic acid
  4. washthe aqueous extracts are washed with ether
  5. extractionextracted with dichloromethane
  6. washThe dichloromethane layer is washed with water
  7. customdried
  8. concentrationconcentrated
  9. customis placed under vacuum overnight (6.8 g, m.p. 63-64° C.)

Sources & evidence

ORD record
ord-0f4211eea2da482084bb4d5b8636d77a
Source dataset
uspto-grants-2001_09
Patent number
US06291463B1

Reaction notes

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