Sodium Iodide → N-(t-butoxycarbonyl)-N'-cyclohexyl-N'-methylethylenediamine

HRID 1581810노트

반응식

HRID 1581810 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10]Br)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:12][NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:13]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 7514N-MethylcyclohexylamineHCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

생성물 1

HCID 22722898N-(t-butoxycarbonyl)-N'-cyclohexyl-N'-methylethylenediamine수율 72%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-(t-butoxycarbonyl)-2-bromoethylamine (1.0 g) in anhydrous dimethylformamide (15 ml) are added N-methylcyclohexylamine (0.64 ml), anhydrous potassium carbonate (0.9 g) and sodium iodide (2.0 g), and the mixture is stirred at room temperature for three days. Water is added to the reaction mixture, and the whole is extracted with ether. The organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution, water and saturated brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography to give 0.82 g (72%) of N-(t-butoxycarbonyl)-N′-cyclohexyl-N′-methylethylenediamine as oily matter.

후처리

  1. extractionthe whole is extracted with ether
  2. washThe organic layer is washed with a 10% aqueous sodium hydrogencarbonate solution, water and saturated brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-685a394c721849cdba65bf1296958970
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06730784B2

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