Dichloromethane → 1-(4-Ethoxy-6-methyl-2-pyridyl)piperazine hydrochloride

HRID 1775376Notes

Reaction equation

HRID 1775376 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[CH:5]=1)[CH3:2].C(Cl)[Cl:25]>FC(F)(F)/C=C/C(O)=O>[ClH:25].[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([N:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 131734740tert-Butyl 4-(4-ethoxy-6-methyl-2-pyridyl)piperazine-1-carboxylate

Product 1

HCID 898258231-(4-Ethoxy-6-methyl-2-pyridyl)piperazine hydrochloride

Reagents, catalysts & solvents 1

HCID 57096144,4,4-Trifluorocrotonic acidSolvent

Procedure

tert-Butyl 4-(4-ethoxy-6-methyl-2-pyridyl)piperazine-1-carboxylate (141 mg, 0.44 mmol) was dissolved in a mixture of DCM (5 ml) and trifluorocrotonic acid (5 ml) and left standing at room temperature for two hours. The mixture was concentrated under reduced pressure, the residue was dissolved in THF, evaporated again, dissolved again in THF. Hydrochloric acid (4N in dioxane) was added to precipitate the product, which was collected by filtration, washed with diethylether and dried under reduced pressure to give 115 mg (quantitative) MS (multi-mode) m/z=222.2 [M+H]+.

Workup

  1. waitleft
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in THF
  4. customevaporated again
  5. dissolutiondissolved again in THF
  6. additionHydrochloric acid (4N in dioxane) was added
  7. customto precipitate the product, which
  8. filtrationwas collected by filtration
  9. washwashed with diethylether
  10. customdried under reduced pressure
  11. customto give 115 mg (quantitative)

Sources & evidence

ORD record
ord-f933a801f41a47999eee4777ae947b5f
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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