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

HRID 2297700ノート

反応式

HRID 2297700 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0661d0e8c8da47209f1e8e5289cabb4e
出典データセット
uspto-grants-2002_12
特許番号
US06492370B1

反応ノート

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