Dichloromethane → HCID 89825932, compound

HRID 1775366Notes

Reaction equation

HRID 1775366 reaction equation
[F:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:21])[CH:3]=1.C(Cl)[Cl:23]>FC(F)(F)C(O)=O>[ClH:23].[F:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 131734739HCID 131734739, compound

Product 1

HCID 89825932HCID 89825932, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(6-fluoro-4-methyl-2-pyridyl)piperazine-1-carboxylate (360 mg, 1.22 mmol) was dissolved in a mixture of DCM (20 ml) and trifluoroacetic acid (5 ml) and stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure, dissolved in THF, evaporated again and again dissolved in THF. Hydrochloric acid (4N in dioxan) was added, the precipitate was collected by filtration, washed with THF and dried under reduced pressure to give 265 mg of a solid (1.14 mmol, yield 93%) MS (multi-mode) m/z=196.1 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutiondissolved in THF
  3. customevaporated again
  4. dissolutionagain dissolved in THF
  5. additionHydrochloric acid (4N in dioxan) was added
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with THF
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-f742a2cd010349e8903c029d89a807b5
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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