Hydrochloric Acid → 2-(4-Cyclopropylpiperazin-1-yl)benzothiazol-6-ylamine

HRID 1619257Notes

Reaction equation

HRID 1619257 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([NH:19]C(=O)C)[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>CCO>[CH:1]1([N:4]2[CH2:5][CH2:6][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:8][CH2:9]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23728857N-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-yl]acetamide

Product 1

HCID 595888042-(4-Cyclopropylpiperazin-1-yl)benzothiazol-6-ylamineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-[2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-yl]-acetamide (679 mg, 2.15 mmol) in EtOH (36 mL) was added concentrated hydrochloric acid (7.2 mL). The mixture was heated at reflux for 2 h. After cooling, the mixture was neutralized with 15% sodium hydroxide. The volatiles were removed under reduced pressure and the residue was dissolved in methanol (10 mL). The mixture was filtered and the filtrate was concentrated in vacuo to give 512 mg (87%) of 2-(4-cyclopropylpiperazin-1-yl)benzothiazol-6-ylamine.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. customThe volatiles were removed under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (10 mL)
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0416961939c14510bf6bae50fdc20221
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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