Chlorosuccinimide → 1-(4-Chloromethyl-5-methyl-1,3-thiazol-2-yl)piperidine

HRID 2221556노트

반응식

HRID 2221556 반응식
[CH3:1][C:2]1[N:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[S:5][C:6]=1[CH3:7].[Cl:14]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:14][CH2:1][C:2]1[N:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[S:5][C:6]=1[CH3:7]

참가 물질

5

반응물 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 230765394,5-Dimethyl-2-(piperidin-1-yl)thiazole

생성물 1

HCID 230765561-(4-Chloromethyl-5-methyl-1,3-thiazol-2-yl)piperidine수율 14.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 1-(4,5-dimethyl-1,3-thiazol-2-yl)piperidine (4.00 g) in acetonitrile (100 mL) was added N-chlorosuccinimide (2.72 g) at room temperature, and the mixture was stirred at the same temperature for 15 hrs. After concentration of the reaction mixture, saturated aqueous sodium hydrogen carbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 1-(4-chloromethyl-5-methyl-1,3-thiazol-2-yl]piperidine as colorless crystals (0.67 g, yield 14%) from a fraction eluted with ethyl acetate-hexane (1:8, v/v). Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 79-80° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ca35b76c282341878e951e60dbf61e86
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368578B2

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