Water → tert-butyl 4-(4-chloro-2-formylphenyl)tetrahydro-1(2H)-pyrazinecarboxylate

HRID 504540Notes

Reaction equation

HRID 504540 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][N:21]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27735865-Chloro-2-fluorobenzaldehyde

Product 1

HCID 11529912tert-butyl 4-(4-chloro-2-formylphenyl)tetrahydro-1(2H)-pyrazinecarboxylateYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 5-chloro-2-fluoro-benzaldehyde (10 g, 63 mmol), Piperazine-1-carboxylic acid tert-butyl ester (12 g, 63 mmol), K2CO3 (17 g, 123 mmol) in DMF (60 mL) was heated at 150° C. for 2 h. After cooled to room temperature, the mixture was poured into water (300 mL) and partitioned between diethyl ether and water. The combined organic phases were washed with water, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column to give the title compound as a yellow solid (9 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. custompartitioned between diethyl ether and water
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-25fd46b1a99e48199927a7181095e165
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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