Hydrochloric Acid → 3'-(4-Ethoxyphenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

HRID 220433Notes

Reaction equation

HRID 220433 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1.C(Cl)Cl>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]2[C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:15][CH:16]=[CH:17][N:18]=2)=[CH:21][CH:22]=1)[CH3:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 687387893'-(4-Ethoxyphenyl)-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carboxylic acid t-butyl ester

Product 1

HCID 685953423'-(4-Ethoxyphenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Deprotect 3′-(4-ethoxyphenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid t-butyl ester (1.80 g, 4.7 mmol) using 4 M HCl in 1,4-dioxane (38 mL) in DCM (100 mL). Concentrate and dissolve the residue in DCM and 10% aqueous sodium carbonate. Separate the layers and extract the aqueous layer with DCM (2×150 mL). Combine the organic layers, wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give the title preparation (1.12 g, 84%). MS (ES): m/z=285 [M+H]+.

Workup

  1. concentrationConcentrate
  2. dissolutiondissolve the residue in DCM
  3. customSeparate the layers
  4. extractionextract the aqueous layer with DCM (2×150 mL)
  5. washCombine the organic layers, wash with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate
  8. customto give the title
  9. custompreparation (1.12 g, 84%)

Sources & evidence

ORD record
ord-e4a87284759b4bfeb9ae0b91076831e0
Source dataset
uspto-grants-2012_06
Patent number
US08202873B2

Reaction notes

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