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

HRID 2221556ノート

反応式

HRID 2221556 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca35b76c282341878e951e60dbf61e86
出典データセット
uspto-grants-2008_05
特許番号
US07368578B2

反応ノート

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