1-(2-Methoxyphenyl)piperazine → (R)-1-(2-Methoxyphenyl)-4-[2-(methyl)-2-(2-pyridinylamino)ethyl]piperazine

HRID 566589노트

반응식

HRID 566589 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH3:15][C@@H:16]1[CH2:20]OS(=O)(=O)[N:17]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([CH3:20])[NH:17][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:11][CH2:10]1

참가 물질

4

반응물 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 22863100(R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide

생성물 1

HCID 25273062(R)-1-(2-Methoxyphenyl)-4-[2-(methyl)-2-(2-pyridinylamino)ethyl]piperazine수율 77.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

12.02 grams of 1-(2-methoxyphenyl)piperazine and 13.4 grams of (R)-4-methyl-3-pyridin-2-yl[1,2,3]oxathiazolidine-2,2-dioxide were stirred together in 50 millilitres of acetonitrile at room temperature overnight. The solvent was removed in vacuo. The residue was heated in 100 millilitres of dilute hydrochloric acid for 30 minutes. The mixture was cooled, washed with dichloromethane, basified by using dilute sodium hydroxide solution and extracted by means of dichloromethane. The organic phase was washed with water, dried and evaporated to dryness to give 15.8 g of the title compound as a slightly crude product. The product was 85 to 95% pure and contained 2 main impurities derived from the sulphone. The crude product was used directly, i.e. without purification, by acylation by means of cyclohexanecarbonyl chloride to yield (R)-N-[1-methyl-2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl) cyclohexanecarboxamide.

후처리

  1. customThe solvent was removed in vacuo
  2. temperatureThe residue was heated in 100 millilitres of dilute hydrochloric acid for 30 minutes
  3. temperatureThe mixture was cooled
  4. washwashed with dichloromethane
  5. extractionextracted by means of dichloromethane
  6. washThe organic phase was washed with water
  7. customdried
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-57eee1fbc18f461a9ac7d450376aeee5
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06175012B1

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