p-Toluenesulfonic acid → tert-butyl 4-(1-acetyl-1H-indol-3-yl)piperazine-1-carboxylate

HRID 641887

反応式

HRID 641887 の反応式
C(O[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14](=[O:16])[CH3:15])[CH:6]=1)(=O)C.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:14]([N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([N:20]2[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]2)=[CH:6]1)(=[O:16])[CH3:15]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5836021-Acetyl-1H-indol-3-yl acetate

生成物 1

HCID 59259291tert-butyl 4-(1-acetyl-1H-indol-3-yl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

Into a 150 mL sealed tube was placed a solution of 1-acetyl-1H-indol-3-yl acetate (2.5 g, 11.51 mmol) in toluene (80 mL). To this was added tert-butyl piperazine-1-carboxylate (10.71 g, 57.55 mmol). To the mixture was added p-toluenesulfonic acid (400 mg, 2.33 mmol). The resulting solution was allowed to react, with stirring, overnight while the temperature was maintained at 120° C. in a bath of oil. The reaction progress was monitored by TLC (ethyl acetate/petroleum ether=1:1). The mixture was concentrated by evaporation under vacuum using a rotary evaporator. The resulting solution was diluted with 200 mL of ethyl acetate. The resulting mixture was washed 3 times with 200 mL of NaCl(aq.). The mixture was dried over Na2SO4. The residue was purified by eluting through a column with a 10:1 petroleum ether/ethyl acetate solvent system. This resulted in 2.9 g (72%) of tert-butyl 4-(1-acetyl-1H-indol-3-yl)piperazine-1-carboxylate as a purple solid.

後処理

  1. customInto a 150 mL sealed tube
  2. customto react
  3. concentrationThe mixture was concentrated by evaporation under vacuum
  4. customa rotary evaporator
  5. additionThe resulting solution was diluted with 200 mL of ethyl acetate
  6. washThe resulting mixture was washed 3 times with 200 mL of NaCl(aq.)
  7. dry with materialThe mixture was dried over Na2SO4
  8. customThe residue was purified
  9. washby eluting through a column with a 10:1 petroleum ether/ethyl acetate solvent system
  10. customThis resulted in 2.9 g (72%) of tert-butyl 4-(1-acetyl-1H-indol-3-yl)piperazine-1-carboxylate as a purple solid

出典と根拠

ORDレコード
ord-aac31a08a2a542ecaefc79b1615cad5f
出典データセット
uspto-grants-2010_04
特許番号
US07696229B2

関連ノート

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