Water → N-(1H-indol-1-yl)-N-propylcarbamic acid ethyl ester

HRID 2051203ノート

反応式

HRID 2051203 の反応式
[CH2:1]([O:3][C:4](=[O:15])[NH:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].[CH3:16][C:17](C)([O-])[CH3:18].[K+].BrCCC.O>O1CCCC1>[CH2:1]([O:3][C:4](=[O:15])[N:5]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH2:16][CH2:17][CH3:18])[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 78401-BromopropaneHCID 10512386N-(1H-indol-1-yl) carbamic acid ethyl esterHCID 23665647Potassium tert-butoxide

生成物 1

HCID 10514581N-(1H-indol-1-yl)-N-propylcarbamic acid ethyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
5 °C

実験手順

To a suspension of NaHCO3 (50 g, 0.7 mole) in 100 ml dichloromethane (DCM) was added a solution of 1H-indol-1-amine (36 g, 0.27 mole) in 200 ml DCM. After cooling to 0° C. with an ice bath, a solution of ethyl chloroformate (29 ml, 0.30 mole) in 50 ml DCM was added over a period of thirty minutes. After stirring at ambient temperature for three hours, the mixture was filtered, and the filtrate washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil which was eluted on a silica gel column with DCM, via high performance liquid chromatography (HPLC) to give N-(1H-indol-1-yl) carbamic acid ethyl ester, 33.6 g (61%) as an oil. To a cold solution of N-(1H-indol-1-yl) carbamic acid ethyl ester (15 g, 0.07 mole) in 100 ml tetrahydrofuran, was added potassium t-butoxide (9 g, 0.08 mole), and the mixture stirred at 5° C. for one hour. To this was added 1-bromopropane (7.3 ml, 0.08 mole), and the mixture stirred at ambient temperature for five hours. The mixture was poured into 300 ml iced-water, stirred for five minutes, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated, NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to give N-(1H-indol-1-yl)-N-propylcarbamic acid ethyl ester as an oil, 16.5 g (91%). To a solution of N-(1H-indol-1-yl)-N-propylcarbamic acid ethyl ester (16.5 g, 0.067 mole) in 35 ml ethylene glycol, was added a solution of NaOH (10 g, 0.25 mole) in 30 ml water. After stirring at 120° C. for four hours, the mixture was poured into 300 ml ice water, stirred for five minutes, then extracted with ethyl acetate. The organic layer was washed with water, then dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to give N-(1H-indol-1-yl)-N-propylamine, 9.0 g (78%) as an oil.

後処理

  1. stirringthe mixture stirred at ambient temperature for five hours
  2. stirringstirred for five minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (saturated, NaCl, anhydrous MgSO4)
  6. filtrationAfter filtering
  7. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-3b838a5d0fba4bda924205d58e985b65
出典データセット
uspto-grants-1991_05
特許番号
US05017578

反応ノート

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