1-Phenylpiperazine → HCID 9948518, 화합물

HRID 1838205노트

반응식

HRID 1838205 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 9948518HCID 9948518, 화합물수율 21.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-14148458fa44435c86d8156ad9abda3c
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06673795B2

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