Trifluoroacetic acid → 2-(3-Methylphenyl)-3-(piperazin-1-yl)pyrazine

HRID 220419Notes

Reaction equation

HRID 220419 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:22]1([CH3:26])[CH:23]=[CH:24][CH:25]=[C:20]([C:19]2[C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:15][CH:16]=[CH:17][N:18]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 687368123'-m-Tolyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl ester

Product 1

HCID 685957832-(3-Methylphenyl)-3-(piperazin-1-yl)pyrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 3′-m-tolyl-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (3.3 g, 9.32 mmol) in DCM (10 mL). Add cold (from refrigerator) trifluoroacetic acid (42.6 g, 28.8 mL). Stir for 2 hr. at room temperature. Partition reaction mixture between methylene chloride and 5N NaOH (pH aqueous=14). Separate layers. Extract aqueous layer with methylene chloride (2×20 mL). Combine organic layers, dry over anh. sodium sulfate, filter and concentrate to give the title preparation (2.35 g, 99%). MS (ES): m/z=255 [M+H]+.

Workup

  1. customat room temperature
  2. customPartition
  3. customreaction mixture between methylene chloride and 5N NaOH (pH aqueous=14)
  4. dry with materialCombine organic layers, dry over anh. sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customto give the title
  8. custompreparation (2.35 g, 99%)

Sources & evidence

ORD record
ord-d096f6dabe5c46298550049854c5b1c3
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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