Preparation method of high allylamine compound promoted by visible light and water
A technology for high allyl amines and compounds, which is used in pharmaceutical and chemical intermediates and related chemical fields, can solve the problems of low total yield, harsh reaction conditions, and small scope of application of substrates, and achieves mild reaction conditions and substrates. Good compatibility, simple operation and post-processing effects
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0023] Example 1: Synthesis of 1-allyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline
[0024] Accurately weighed N-phenyl-1,2,3,4-tetrahydroisoquinoline (41.8mg, 0.2mmol), potassium allyl trifluoroborate (59.2mg, 0.4mmol) were added to 25mL of Schlenk reaction In the bottle, add 1.0 mL of water in a mixed organic solvent of acetonitrile and tetrahydrofuran (MeCN / THF=2:1, 1.5 mL), and place under light conditions (3W×6blue LEDs) to react at room temperature for 12h. After the reaction, the solvent was removed under reduced pressure, and the product was separated by silica gel column using petroleum ether / dichloromethane as the eluent, and the yield of the product was 80%.
[0025]
[0026] 1-Allyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline
[0027] 1 H NMR (400MHz, CDCl 3 )δ7.24–7.22(m,2H),7.17–7.10(m,4H),6.89(d,J=8.2Hz,2H),6.75–6.71(m,1H),5.90–5.80(m,1H) , 5.08–5.03 (m, 2H), 4.74 (t, J=6.8Hz, 1H), 3.67–3.56 (m, 2H), 3.06–2.99 (m, 1H), 2.91–2.84 (m, 1H), 2.77 –2.70(m,1H),2.52–2....
Embodiment 2
[0028] Example 2: Synthesis of 1-allyl-2-m-tolyl-1,2,3,4-tetrahydroisoquinoline
[0029] Accurately weigh 2-m-tolyl-1,2,3,4-tetrahydroisoquinoline (44.6 mg, 0.2 mmol) and potassium allyl trifluoroborate (59.2 mg, 0.4 mmol) and add them to 25 mL of Schlenk In the reaction flask, add 1.0 mL of water in a mixed organic solvent of acetonitrile and tetrahydrofuran (MeCN / THF=2:1, 1.5 mL), and place it under illumination (3W×6blue LEDs) to react at room temperature for 12h. After the reaction, the solvent was removed under reduced pressure, and the product was separated by silica gel column using petroleum ether / dichloromethane as the eluent, and the yield of the product was 69%.
[0030]
[0031] 1-Allyl-2-m-tolyl-1,2,3,4-tetrahydroisoquinoline
[0032] 1 H NMR (400MHz, CDCl 3 )δ7.21–7.10(m,5H),6.71–6.69(m,2H),6.58–-6.55(m,1H),5.91–5.80(m,1H),5.08–5.02(m,2H),4.76 –4.72 (m, 1H), 3.66–3.54 (m, 1H), 3.06–2.98 (m, 1H), 2.89–2.82 (m, 1H), 2.76–2.69 (m, 1H), 2.52–2.44 (m, 1H), 2.3...
Embodiment 3
[0033] Example 3: Synthesis of 1-allyl-2-p-tolyl-1,2,3,4-tetrahydroisoquinoline
[0034] Accurately weigh 2-m-tolyl-1,2,3,4-tetrahydroisoquinoline (44.6 mg, 0.2 mmol) and potassium allyl trifluoroborate (59.2 mg, 0.4 mmol) and add them to 25 mL of Schlenk In the reaction flask, 1.0 mL of water was added to the solvent of acetonitrile (1.5 mL), and the reaction was performed at room temperature for 12 h under light conditions (3W×6 blue LEDs). After the reaction, the solvent was removed under reduced pressure, and the product was separated by silica gel column using petroleum ether / dichloromethane as the eluent, and the yield of the product was 87%.
[0035]
[0036] 1-Allyl-2-p-tolyl-1,2,3,4-tetrahydroisoquinoline
[0037] 1 H NMR (400MHz, CDCl 3 )δ7.15–7.09(m,4H),7.05–7.02(m,2H),6.83–6.79(m,2H),5.90–5.80(m,1H),5.06–5.01(m,2H),4.69( t, J=6.8Hz, 1H), 3.60-3.56(m,1H), 3.04-2.96(m,1H), 2.85-2.78(m,1H), 2.73-2.66(m,1H), 2.51-2.44( m,1H),2.24(s,3H).
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More