Ammonium Chloride → 2-(4-Cyclopropylpiperazin-1-yl)benzothiazole-6-carbonitrile

HRID 1619245Notes

Reaction equation

HRID 1619245 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:13]1([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:15][CH2:14]1.[Cl-].[NH4+]>C(O)CCC>[CH:13]1([N:16]2[CH2:21][CH2:20][N:19]([C:2]3[S:3][C:4]4[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=4[N:6]=3)[CH2:18][CH2:17]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 47420041-CyclopropylpiperazineHCID 219858592-Chloro-1,3-benzothiazole-6-carbonitrile

Product 1

HCID 595887892-(4-Cyclopropylpiperazin-1-yl)benzothiazole-6-carbonitrileYield 43%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 2-chlorobenzothiazole-6-carbonitrile (3.5 g, 18 mmol), 1-cyclopropyl-piperazine (3.63 g, 28.8 mmol) and ammonium chloride (0.96 g, 18 mmol) in butan-1-ol (112 mL) was heated at reflux for 48 h. The solvent was removed under reduced pressure and the residue was diluted with water (30 mL). The mixture was made alkaline with potassium carbonate and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were concentrated to give a residue which was purified by column chromatography on silica gel (20% ethyl acetate in petroleum ether) to give 2.2 g (43 5) of 2-(4-cyclopropylpiperazin-1-yl)-benzothiazole-6-carbonitrile.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue was diluted with water (30 mL)
  5. extractionextracted with CH2Cl2 (3×20 mL)
  6. concentrationThe combined organic extracts were concentrated
  7. customto give a residue which
  8. customwas purified by column chromatography on silica gel (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-3cc136eb8c884c6b9ef4577dc0b9be1b
Source dataset
uspto-grants-2014_07
Patent number
US08772285B2

Reaction notes

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