Dichloromethane → 2-(Piperazin-1-yl)quinoline hydrochloride

HRID 1775329Notes

Reaction equation

HRID 1775329 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[N:2]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:32]>>[ClH:32].[N:11]1([C:3]2[CH:4]=[CH:5][C:10]3[C:1](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:2]=2)[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57690803tert-Butyl 4-(isoquinolin-3-yl)piperazine-1-carboxylate

Product 1

HCID 529881592-(Piperazin-1-yl)quinoline hydrochloride

Procedure

To tert-butyl 4-(3-isoquinolyl)piperazine-1-carboxylate (201 mg, 0.64 mmol) was added a 1:1 mixture of DCM and trifluoroacetic acid, the resulting mixture was stirred at room temperature for one hour. The volatiles were removed under reduced pressure, the residue was dissolved in THF and evaporated again. The residue was dissolved in THF and 4N HCl in 1,4-dioxane was added to precipitate the hydrochloride salt which was collected by filtration and dried under reduced pressure. 123 mg of a solid were obtained (0.49 mmol, 77%). MS (APCI) m/z=214.1 [M+1]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue was dissolved in THF
  3. customevaporated again
  4. dissolutionThe residue was dissolved in THF
  5. addition4N HCl in 1,4-dioxane was added
  6. customto precipitate the hydrochloride salt which
  7. filtrationwas collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-d0fc8036aa5e422e9d72f1a02394fb9c
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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