3-Cyclohexene-1-carbonyl chloride → HCID 57004125, 화합물

HRID 963259

반응식

HRID 963259 반응식
[CH3:1][C@@H:2]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:3][N:4]1[CH2:9][CH:8]=[C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5]1.[CH:22]1([C:28](Cl)=[O:29])[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1>C(Cl)Cl>[CH3:1][C@@H:2]([N:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[C:28]([CH:22]1[CH2:27][CH2:26][CH:25]=[CH:24][CH2:23]1)=[O:29])[CH2:3][N:4]1[CH2:5][CH:6]=[C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:9]1

참가 물질

4

반응물 2

HCID 5230583-Cyclohexene-1-carbonyl chlorideHCID 18660712(R)-[1-Methyl-2-(4-thiophen-2-yl-1,2,3,6-tetrahydropyrid-1-yl)ethyl]-pyrid-2-yl-amine

생성물 1

HCID 57004125HCID 57004125, 화합물수율 44.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of the starting (R)-[1-methyl-2-(4-thiophen-2-yl-3,6-dihydro-2H-pyrid-1-yl)-ethyl]-pyrid-2-yl-amine (0.46 g, 1.5 mmol) in methylene chloride (20 ml) was cooled to 0° C., after which a solution of cyclohex-3-enecarbonyl chloride (0.222 g, 1.5 mmol) in methylene chloride (10 ml) was dropwise added under exclusion of moisture. The reaction mixture was stirred at ambient temperature overnight, then washed with 2.5N NaOH (10 ml). The separated organic layer was washed with brine (50 ml), dried over magnesium sulfate, filtered, and evaporated to dryness in vacuo. Column chromatography on 50 g of silica gel with chloroform as eluant, followed by trituration in ether with the addition of ethanolic HCl gave 0.27g of the title compound as the dihydrochloride, m.p. 92°-6° C.

후처리

  1. washwashed with 2.5N NaOH (10 ml)
  2. washThe separated organic layer was washed with brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. additionColumn chromatography on 50 g of silica gel with chloroform as eluant, followed by trituration in ether with the addition of ethanolic HCl

출처 및 근거

ORD 기록
ord-e997d55740634178bf491cfc3d1247a7
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05763460

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