반응 #816417

반응 방정식

14

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

trifluoroacetic acid

trifluoroacetic anhydride

→

compound 15

수율 94.0%

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

수율 94.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   온도cooled
2. 2
   workup.ADDITIONthe mixture is poured onto ice
3. 3
   추출extracted twice with CH2Cl2
4. 4
   기타evaporated
5. 5
   기타The mixture is chromatographed on silica gel

실험 절차

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).

출처