1-Phenylpiperazine → 2-[2-(4-Phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione

HRID 1516781ノート

反応式

HRID 1516781 の反応式
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][CH2:15][N:16]1[C:20](=[O:21])[C:19]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]2[C:17]1=[O:26].CCN(CC)CC.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:14][CH2:15][N:16]3[C:20](=[O:21])[C:19]4=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]4[C:17]3=[O:26])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium Carbonate

生成物 1

HCID 85979842-[2-(4-Phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 1-phenylpiperazine 2 (2.59 g, 15.98 mmol) was reacted with N-(2-bromoethyl)phthalimide (8.12 g, 31.96 mmol), Et3N (2.0 mL) and K2CO3 (8.0 g) in DMF (40 mL) and stirred at 70° C. under N2 overnight. After the reaction mixture was cooled down, water (100 mL) was added. The mixture was extracted with diethyl ether. The organic phase was combined and dried over Na2SO4. The solvent was removed under vacuo to give the crude product, which was purified by flash chromatography (Hexane/EtOac=1/1) to furnish 3a, 3.81 g (71%) 1HNMR (CDCl3) 2.68-2.72 (m, 6H, N(CH2)2, CONCH2), 3.12-3.15 (t, J=4.8 Hz, 4H, N(CH2)2), 3.84-3.89 (t, J=6.3 Hz, 2H), 6.80-6.82 (t, J=8.1 Hz, 1H, Ar—H), 6.88-6.91 (d, J=8.1 Hz, 2H, Ar—H), 7.21-7.26 (t, J=8.1 Hz, 2H, Ar—H), 7.69-7.86 (m, 4H, Ar—H).

後処理

  1. temperatureAfter the reaction mixture was cooled down
  2. extractionThe mixture was extracted with diethyl ether
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under vacuo
  5. customto give the crude product, which
  6. customwas purified by flash chromatography (Hexane/EtOac=1/1)

出典と根拠

ORDレコード
ord-212ab999091d470f8665a510ab941233
出典データセット
uspto-grants-2012_07
特許番号
US08227604B2

反応ノート

読み込み中…