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

HRID 1417833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1417833
[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

Komponenten

10

Edukt 6

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 174Ethylene GlycolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6dcce1f5c79041e1bea1eab68d316846
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877317

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