1-Phenylpiperazine → HCID 9948518, compound

HRID 1838205Notes

Reaction equation

HRID 1838205 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:9]([C:17]#[N:18])=[N:10][C:11]([CH2:15][CH3:16])=[C:12]([CH3:14])[N:13]=1.ClC1C(C#N)=NC(C)=C(CC)N=1.[C:31]1([N:37]2[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O>[CH2:15]([C:11]1[N:10]=[C:9]([C:17]#[N:18])[C:8]([N:40]2[CH2:41][CH2:42][N:37]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:38][CH2:39]2)=[N:13][C:12]=1[CH3:14])[CH3:16]

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 111596793-Chloro-5-ethyl-6-methyl-2-pyrazinecarbonitrileHCID 11355861HCID 11355861, compound

Product 1

HCID 9948518HCID 9948518, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.416 mg (3.0 mmol) of potassium carbonate were added to a solution of 0.182 g (1.0 mmol) of the 1:1 mixture of the 3-chloro-6-ethyl-5-methyl-pyrazine-2-carbonitrile and the 3-chloro-5-ethyl-6-methyl-pyrazine-2-carbonitrile and of 0.199 g (1.2 mmol) of 1-phenylpiperazine in 10.0 ml of N,N-dimethylformamide and the reaction mixture was stirred at room temperature for 16 hours. It was subsequently poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 4:1 to 0:100 v/v gradient of hexane and dichloromethane as the eluent giving 0.067 g (0.218 mmol, 21.8% of theory) of the 5′-ethyl-6′-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-carbonitrile as orange oil; MS: 308 (M+H)+; and 0.043 g (0.14 mmol, 14% of theory) of the 6′-ethyl-5′-methyl-4-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-carbonitrile as yellow solid; m.p. 99-101° C.; MS: 308 (M+H)+.

Workup

  1. extractionextracted 3 times with 50 ml of dichloromethane
  2. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue formed
  5. customwas chromatographed on silica gel with a 4:1 to 0:100 v/v gradient of hexane and dichloromethane as the eluent

Sources & evidence

ORD record
ord-14148458fa44435c86d8156ad9abda3c
Source dataset
uspto-grants-2004_01
Patent number
US06673795B2

Reaction notes

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