تفاعل #816417

معادلة التفاعل

14

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

trifluoroacetic acid

trifluoroacetic anhydride

→

compound 15

المردود 94.0%

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

المردود 94.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled
2. 2
   workup.ADDITIONthe mixture is poured onto ice
3. 3
   استخلاصextracted twice with CH2Cl2
4. 4
   أخرىevaporated
5. 5
   أخرىThe mixture is chromatographed on silica gel

الإجراء التجريبي

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).

المصدر