Triethylamine → 2,2-Dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

HRID 249328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249328
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1.CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]([CH3:7])([CH3:6])[C:3]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16]1)=[O:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 197614202-(2-Aminophenyl)-2,3-dihydro-1H-indole

Produkt 1

HCID 197613982,2-Dimethyl-N-[2-(2,3-dihydro-1H-indol-2-yl)phenyl]propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trimethylacetyl chloride (3.6 ml) was added dropwise to a solution of 5.8 g 2-(2-aminophenyl)-2,3-dihydro-1H-indole and 4.3 ml Et3N in 75 ml CH2Cl2 with ice bath cooling. The resulting mixture was stirred at room temperature for thirty minutes and then quenched with water. The organic extract was washed with water, saturated NaHCO3 solution and saturated NaCl solution and dried (MgSO4). Concentration gave 7.7 g crude product which was flash chromatographed using CH2Cl2 as eluent to give 4.9 g solid, m.p. 175°-178° C.

Aufarbeitung

  1. temperaturecooling
  2. customquenched with water
  3. extractionThe organic extract
  4. washwas washed with water, saturated NaHCO3 solution and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration
  7. customgave 7.7 g crude product which
  8. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-88f6ffffef93490b8b8fcdd8d93b0e51
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05214059

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