Trifluoroacetic acid → 2-Chloro-6-(1-piperazinyl)pyrazine

HRID 1357578Notes

Reaction equation

HRID 1357578 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[C:13]([N:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH:12]=[N:11][CH:10]=1.[OH-].[Na+]>ClCCl>[Cl:8][C:9]1[N:14]=[C:13]([N:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[CH:12]=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 14798Sodium HydroxideHCID 18186946Tert-butyl 4-(6-chloropyrazin-2-YL)piperazine-1-carboxylate

Product 1

HCID 1079922-Chloro-6-(1-piperazinyl)pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trifluoroacetic acid (TFA; 6 mL) in dichloromethane (24 mL) was added to a stirred solution of the product of step 1 above (5.79 g, 19.4 mmol) in dichloromethane (20 mL) at 0° C. After 1 h and 1.5 h of stirring, additional portions (10 mL and 5 mL) of TFA were added. Crushed ice and 5 M aqueous NaOH were added and the mixture was extracted with dichloromethnae (12×200 mL). The combined organic layers were dried (K2CO3), filtered and concentrated in vacuo. This furnished 3.48 g (90%) of the title compound as a light yellow solid.

Workup

  1. extractionthe mixture was extracted with dichloromethnae (12×200 mL)
  2. dry with materialThe combined organic layers were dried (K2CO3)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e45e6e3f1d9c425187f2e94908e6fbfe
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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