Triethylamine → 4-[2-(Inden-1-yl)ethyl]-1-(4-aminocarbonylphenyl)piperazine

HRID 368852ノート

反応式

HRID 368852 の反応式
[CH:1]1([CH2:10][CH2:11]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CN(C1C=CC=CN=1)C.C(N(CC)CC)C.CS(Cl)(=O)=O.[N:34]1([C:40]2[CH:45]=[CH:44][C:43]([C:46]([NH2:48])=[O:47])=[CH:42][CH:41]=2)[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(N(C(C)C)CC)(C)C>O1CCCC1.O.C(O)CO>[CH:1]1([CH2:10][CH2:11][N:37]2[CH2:36][CH2:35][N:34]([C:40]3[CH:41]=[CH:42][C:43]([C:46]([NH2:48])=[O:47])=[CH:44][CH:45]=3)[CH2:39][CH2:38]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参加物

10

反応物 6

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 111065094-(1-Piperazinyl)benzamideHCID 232887512-(1H-Inden-1-yl)ethan-1-ol

生成物 1

HCID 232887964-[2-(Inden-1-yl)ethyl]-1-(4-aminocarbonylphenyl)piperazine

試薬・触媒・溶媒 3

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-(inden-1-yl)ethanol (CXVI-B, EXAMPLE 86, 0.8 g, 5 mmol), dimethylaminopyridine (0.02 g, 0.2 mmol) and triethylamine (1.7 ml, 12.5 mmol) in tetrahydrofuran (10 ml) is cooled to 0° and methanesulfonyl chloride (0.43 ml, 5.5 mmol) is added dropwise. After 45 min, 4-(piperazinyl)benzenecarboxamide (LXV, 1.23 g, 6 mmol), diisopropylethylamine (1.0 ml, 6 mmol) and ethyleneglycol (10 ml) are added and heated at 85° for 60 hr. The mixture is diluted with water and extracted with methylene chloride. The organic phase is separated, washed with saline, dried (magnesium sulfate), filtered and concentrated. Crystallization from ethyl acetate gives the title compound, mp 207°; NMR (CDCl3, TMS) 7.75-6.90, 6.28 and 3.39-2.68 δ.

後処理

  1. temperatureis cooled to 0°
  2. temperatureheated at 85° for 60 hr
  3. extractionextracted with methylene chloride
  4. customThe organic phase is separated
  5. washwashed with saline
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-6e96bca7a221445eb84963b10242a22e
出典データセット
uspto-grants-2000_10
特許番号
US06133446

反応ノート

読み込み中…