Piperazine → HCID 12296696, compound

HRID 1854808Notes

Reaction equation

HRID 1854808 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CS[C:9]1[N:10]=[N:11][CH:12]=[CH:13][N:14]=1.C(N(CC)CC)C.C(OCC)(=O)C>C(O)CCC>[N:1]1([C:9]2[N:10]=[N:11][CH:12]=[CH:13][N:14]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 4837PiperazineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 3218393-(Methylsulfanyl)-1,2,4-triazine

Product 1

HCID 12296696HCID 12296696, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

3.45 g (40.1 mmoles) of piperazine is placed in the presence of 1.7 g (13.4 mmoles) of intermediate 2a in 1-butanol. 6.5 ml (47 mmoles) of triethylamine is added and the mixture is heated for 24 hours at 120° C. After concentrating the reaction medium, the residue obtained is taken up with ethyl acetate and washed with water. After drying on MgSC4, the organic phase is concentrated to dryness. The residue obtained is purified by flash chromatography (CH2Cl2-MeOH-NH4OH gradient: 100-0-0 to 90-9-1). 1.52 g of intermediate 5a is obtained in brown oil form (yield: 69%).

Workup

  1. concentrationAfter concentrating the reaction medium
  2. customthe residue obtained
  3. washwashed with water
  4. customAfter drying on MgSC4
  5. concentrationthe organic phase is concentrated to dryness
  6. customThe residue obtained
  7. customis purified by flash chromatography (CH2Cl2-MeOH-NH4OH gradient: 100-0-0 to 90-9-1)

Sources & evidence

ORD record
ord-b694cb8baa18405b9e6d17258255d1a4
Source dataset
uspto-grants-2015_02
Patent number
US08962837B2

Reaction notes

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