Reaktion #816417

Reaktionsgleichung

14

N-acetyl-7-amino-1,2,3,4-tetrahydroisoquinoline

trifluoroacetic acid

trifluoroacetic anhydride

→

compound 15

Ausbeute 94.0%

N-acetyl-7-trifluoroacetamido-1,2,3,4-tetrahydroisoquinoline

Ausbeute 94.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled
2. 2
   workup.ADDITIONthe mixture is poured onto ice
3. 3
   Extraktionextracted twice with CH2Cl2
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe mixture is chromatographed on silica gel

Vorschrift

A solution of 14 (3.0 g, 17 mmol), trifluoroacetic acid (2 ml, 28 mmol) and trifluoroacetic anhydride (4 ml, 28 mmol) in CH2Cl2 is refluxed for 15 minutes, cooled, and the mixture is poured onto ice, extracted twice with CH2Cl2 and evaporated. The mixture is chromatographed on silica gel to give 4.5 g of compound 15 (94% yield). 1H NMR [300 MHz, (CD3)2SO], a 3:2 mixture of amide conformers doubling most signals, δ 11.24 (0.8H, s, NH), 11.21 (1.2H, s, NH), 7.55-7.40 (2H, m, H5.8), 7.22 (0.6H, s, H-6), 7.20 (0.4H, s, H-6), 4.64 (0.8H, s, ArCH2N), 4.57 (1.2H, s, ArCH2N), 3.65 (2H, t, ArCH2CH2N), 2.84 (1.2H, t, ArCH2CH2N), 2.73 (0.8H, t, ArCH2CH2N), 2.06 (1.2H, s, COCH3), 2.05 (1.8H, s COCH3).

Quelle