Gramine → (2,3-dihydro-1H-indol-3-ylmethyl)dimethylamine

HRID 880178

Reaktionsgleichung

Reaktionsgleichung von HRID 880178
C([BH3-])#N.[Na+].[CH3:5][N:6]([CH2:8][C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][CH:10]=1)[CH3:7]>FC(F)(F)C(O)=O>[NH:11]1[C:12]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]([CH2:8][N:6]([CH3:7])[CH3:5])[CH2:10]1

Komponenten

4

Edukt 2

HCID 6890GramineHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 13156058(2,3-dihydro-1H-indol-3-ylmethyl)dimethylamineAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.1 g of sodium cyanoborohydride is gradually added to a solution of 1 g of gramine in 20 ml of trifluoroacetic acid, under argon, cooled in an ice bath, and stirred for half an hour at 0° C. and then for 2 h at ambient temperature. The reaction medium is plunged into 50 g of ice and alkalinized using 30% sodium hydroxide, and is then extracted with four times 30 ml of ethyl acetate. The organic phase is washed with 20 ml of water, dried over anhydrous magnesium sulphate, filtered, and then concentrated to dryness under reduced pressure. After a silica column purification, eluent: 85/15 v/v CH2Cl2/MeOH, 660 mg of (2,3-dihydro-1H-indol-3-ylmethyl)dimethylamine are obtained in the form of a yellow solid, the characteristics of which are the following:

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. extractionalkalinized using 30% sodium hydroxide, and is then extracted with four times 30 ml of ethyl acetate
  3. washThe organic phase is washed with 20 ml of water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customAfter a silica column purification, eluent

Quellen und Nachweise

ORD-Eintrag
ord-ea07b9d4c47e4ae283c595f0d98262c7
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993565B2

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