Ethylenediamine → trans-4-(2-Aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol

HRID 847167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 847167
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]3[O:14][CH:8]3[C:7]=2[CH:15]=1)#[N:2].[CH2:16]([NH2:19])[CH2:17][NH2:18]>C(O)C>[NH2:18][CH2:17][CH2:16][NH:19][C@@H:8]1[C:7]2[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:13])([CH3:12])[C@H:9]1[OH:14]

Komponenten

4

Edukt 2

HCID 3301EthylenediamineHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Produkt 1

HCID 15680853trans-4-(2-Aminoethylamino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-olAusbeute 111,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension of 6-cyano-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-benzopyran (1.2 g, 5.97 mmol) (prepared according to Evans et al., J. Med. Chem., 1983, 26, 1582 and J. Med. Chem., 1986, 29, 2194) in ethanol (7.0 mL), ethylenediamine (2.4 mL, 35.8 mmol) was added at room temperature and the reaction mixture was stirred at room temperature for 36 hours. The solvent was removed under reduced pressure and the residue was further dried by use of vacuum pump to yield the title A compound (1.74 g, >100%) as a colorless foam. This material was used for the next reaction without any purification.

Aufarbeitung

  1. additionwas added at room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was further dried by use of vacuum pump

Quellen und Nachweise

ORD-Eintrag
ord-b5458a96f21d44c1ba60847dd71cb7fa
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05140031

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