Triethylamine → N-(2-n-Propylpentanoyl)-1-aminoindan

HRID 1417513

Reaktionsgleichung

Reaktionsgleichung von HRID 1417513
[C:1](Cl)(=[O:9])[CH:2]([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][CH3:5].[NH2:11][CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.CCN(CC)CC.CCOC(C)=O>C1(C)C=CC=CC=1.O>[CH2:3]([CH:2]([CH2:6][CH2:7][CH3:8])[C:1]([NH:11][CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=[O:9])[CH2:4][CH3:5]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 762402-Propylvaleryl chlorideHCID 123445(+-)-1-Aminoindan

Produkt 1

HCID 11658951N-(2-n-Propylpentanoyl)-1-aminoindanAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of valproyl chloride (1.55 g, 9.6 mmole) in toluene (25 ml) was added dropwise to a stirred and ice-cooled solution of 1-aminoindan (1.47 g, 10.0 mmole) and Et3N (1.11 g, 11 mmole). The mixture was stirred at ambient temperature for 17 hours, EtOAc (60 ml) and water (50 ml) were added and the phases were separated. The organic phase was washed successively with 0.1N HCl (40 ml), 0.1N NaHCO3 (40 ml) and saturated NaCl (40 ml), dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue was treated with hexane (15 ml, 30 min stirring, RT) and filtered. The crude product was crystallized from hexane:EtOAc (70:30 mixture), to give 1.72 g (6.65 mmole, 69%) of a white crystalline solid, mpt: 133°-4° C.

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 17 hours
  2. customthe phases were separated
  3. washThe organic phase was washed successively with 0.1N HCl (40 ml), 0.1N NaHCO3 (40 ml) and saturated NaCl (40 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. additionThe residue was treated with hexane (15 ml, 30 min stirring, RT)
  7. filtrationfiltered
  8. customThe crude product was crystallized from hexane:EtOAc (70:30 mixture)

Quellen und Nachweise

ORD-Eintrag
ord-3382796c255e4f7b808d1075a81a0226
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877218

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