3-(3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PROPAN-1-AMINE synthesis
- Product Name:3-(3,4-DIHYDROISOQUINOLIN-2(1H)-YL)PROPAN-1-AMINE
- CAS Number:5596-87-2
- Molecular formula:C12H18N2
- Molecular Weight:190.28
![1H-Isoindole-1,3(2H)-dione, 2-[3-(3,4-dihydro-2(1H)-isoquinolinyl)propyl]-](/CAS/20210305/GIF/198895-33-9.gif)
198895-33-9
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5596-87-2
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$75.00/100mg
Yield:5596-87-2 74%
Reaction Conditions:
Stage #1: 2-[3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propyl]-2,3-dihydro-1H-isoindole-1,3-dionewith hydrazine hydrate in ethanol at 85; for 4 h;
Stage #2: with hydrogenchloride in ethanol at 100; for 1 h;
Steps:
3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propan- 1-amine - compound BP
2- [3 -(1,2,3 ,4-tetrahydroisoquinolin-2-yl)propylj -2,3 -dihydro- 1 H-isoindole- 1,3 -dione(6.3 g, 15.53 mmol) was dissolved in Ethanol (10 mL) and hydrazine monohydrate (0.757 mL, 15.5 mmol) was added dropwise. The reaction was heated at 85 °C for 2h. Hydrazine monohydrate (0.757 mL, 15.5 mmol) was added and reaction was heated for another 2h at 85°C. Ethanol (5 mL) and HC1 (6N, 15.5 mmol) were added and mixture was heated at 100 °C for lh. The precipitate was filtered off and washed with water. Combined filtrates were basified with 2M aq. Na2CO3 and extracted with TBME to give the title compound (2.96 g, 85% purity, 74%).1H NMR (500 MHz, Chloroform-d) δ 7.13- 7.07 (m, 3H), 7.04- 6.99 (m, 1H), 3.63 (s, 2H), 2.90 (t, J = 5.9 Hz, 2H), 2.80 (t, J = 6.8 Hz, 2H), 2.73 (t, J = 5.9 Hz, 2H), 2.60- 2.55 (m, 2H), 1.75 (p, J = 6.9 Hz, 2H), 1.48 (s, 2H).
References:
WO2016/191658,2016,A1 Location in patent:Paragraph 00673; 00676-00677
91-21-4
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5596-87-2
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$75.00/100mg
