1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(4-Methylpiperazin-1-yl)pent-4-yn-1-one

HRID 1172256

반응식

HRID 1172256 반응식
[C:1]([OH:7])(=O)[CH2:2][CH2:3][C:4]#[CH:5].[CH3:8][N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[CH3:8][N:9]1[CH2:14][CH2:13][N:12]([C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[CH2:11][CH2:10]1

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 224644-Pentynoic acidHCID 531671-MethylpiperazineHCID 757711-Hydroxybenzotriazole

생성물 1

HCID 577138121-(4-Methylpiperazin-1-yl)pent-4-yn-1-one수율 28.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Pentynoic acid (1.03 g) and N-methylpiperazine (1.0 g) was dissolved in 30 mL of DMF, 1.6 g of HOBt was added to the solution at ice temperature under stirring. After the mixture was stirred at same temperature for 15 minutes, additionally 2.3 g of WSC was added, and the solution was stirred at room temperature overnight. The DMF was removed under reduced pressure from the reaction mixture, then water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine 600:20:1) to give 510 mg of 1-(4-methylpiperazin-1-yl)pent-4-yn-1-one as a colorless oil.

후처리

  1. stirringAfter the mixture was stirred at same temperature for 15 minutes
  2. stirringthe solution was stirred at room temperature overnight
  3. customThe DMF was removed under reduced pressure from the reaction mixture
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed
  9. customThe residue was purified by chromatography on silica gel (methylene chloride-methanol-triethylamine 600:20:1)

출처 및 근거

ORD 기록
ord-cdcae26b9923496390ef48b0b23890f5
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834002B2

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