Hydrochloric Acid → HCID 131730289, compound

HRID 1619224Notes

Reaction equation

HRID 1619224 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:12]1([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.C1(C)C=CC=CC=1.O.CS(C)=O>[ClH:1].[Cl:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([N:20]3[CH2:21][CH2:22][N:17]([CH:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)[CH2:18][CH2:19]3)[S:3][C:4]=2[CH:10]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 771762,6-DichlorobenzothiazoleHCID 8064211-Cyclopentylpiperazine

Product 1

HCID 131730289HCID 131730289, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2,6-dichlorobenzothiazole (0.39 g, 1.9 mmol), 1-cyclopentylpiperazine (0.22 g, 1.4 mmol) and dimethylsulfoxide (2.0 mL) was stirred at 130° C. for 23 h. The reaction mixture was allowed to cool and water (50 mL) and potassium carbonate (1 g) was added. The resulting mixture was extracted with a mixture of ethyl acetate and dichloromethane and filtered. The filtrate was separated and the organic extract was washed with brine (2×) and dried (MgSO4). The volatiles were evaporated to give a solid residue which was dissolved into a mixture of ethanol (30 mL) and 1 N hydrochloric acid (2.5 mL). Toluene was added and the mixture was concentrated. Ethanol and toluene was added and the mixture was concentrated again. This afforded a solid which was treated with ethanol (50 mL) and heated to reflux temperature. The resulting mixture was left overnight for crystallization. This afforded after filtration and drying 0.35 g (69%) of 6-chloro-2-(4-cyclopentylpiperazin-1-yl)-benzothiazole, hydrochloride.

Workup

  1. temperatureto cool
  2. extractionThe resulting mixture was extracted with a mixture of ethyl acetate and dichloromethane
  3. filtrationfiltered
  4. customThe filtrate was separated
  5. extractionthe organic extract
  6. washwas washed with brine (2×)
  7. dry with materialdried (MgSO4)
  8. customThe volatiles were evaporated
  9. customto give a solid residue which
  10. concentrationthe mixture was concentrated
  11. additionEthanol and toluene was added
  12. concentrationthe mixture was concentrated again
  13. customThis afforded a solid which
  14. temperatureheated
  15. temperatureto reflux temperature
  16. waitThe resulting mixture was left overnight for crystallization
  17. customThis afforded
  18. filtrationafter filtration
  19. dry with materialdrying 0.35 g (69%) of 6-chloro-2-(4-cyclopentylpiperazin-1-yl)-benzothiazole, hydrochloride

Sources & evidence

ORD record
ord-93953841e2824957a7ba1a8869478484
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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