1,2-phenylenebis(ethane-2,1-diyl) dimethanesulfonate
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With ammonia at 90℃; for 3h; Sealed tube; | 100% |
Stage #1: 1,2-phenylenebis(ethane-2,1-diyl) dimethanesulfonate With ammonia In water; acetonitrile at 100℃; under 2068.65 Torr; for 1h; Stage #2: With hydrogenchloride; water In acetonitrile pH=4; Stage #3: With sodium hydroxide In diethyl ether; water; acetonitrile pH=14; | 81% |
With ammonia In ethanol; water at 80℃; for 0.666667h; Microwave; | 73% |
With ammonia In acetonitrile at 100℃; under 2068.65 Torr; for 1h; Autoclave; | 20% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With hydrogenchloride; palladium 10% on activated carbon In ethanol; water at 20℃; for 48h; | 95% |
3-formyl-2,3,4,5-tetrahydro-1H-3-benzazepine
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 1h; Hydrolysis; Heating; | 77% |
Conditions | Yield |
---|---|
With ammonia; hydrogen; nickel In ethanol at 50℃; under 51714.8 Torr; for 24h; | 60% |
With ammonia; hydrogen; Raney Nickel In methanol at 70℃; under 36201.3 Torr; for 48h; | 47% |
In ethanol; dichloromethane | 35% |
1,2-phenylenediacetonitrile
A
2,3,4,5-tetrahydro-1H-3-benzazepine
B
2,2'-o-phenylene-bis-ethylamine
Conditions | Yield |
---|---|
With ethanol; ammonia; nickel under 51485.6 Torr; Hydrogenation; |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With ethanol; sodium |
ethanol
ammonia
1,2-phenylenediacetonitrile
A
2,3,4,5-tetrahydro-1H-3-benzazepine
B
2,2'-o-phenylene-bis-ethylamine
Conditions | Yield |
---|---|
unter Druck.Hydrogenation; |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 63 percent / Na2CO3; NaI; tetrabutylammonium bromide / dioxane / Heating 2: 99 percent / acetic anhydride / 1 h / 60 °C 3: 92 percent / aq. NaIO4 / methanol / 1.5 h / 20 °C 4: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 5: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 6: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme |
N-(2-phenylethyl)-2-phenylsulfanylethylamine
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 99 percent / acetic anhydride / 1 h / 60 °C 2: 92 percent / aq. NaIO4 / methanol / 1.5 h / 20 °C 3: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 4: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 5: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme |
N-(2-phenylethyl)-N-(2-phenylsulfanylethyl)formamide
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 92 percent / aq. NaIO4 / methanol / 1.5 h / 20 °C 2: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 3: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 4: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme |
3-formyl-1-phenylsulfanyl-2,3,4,5-tetrahydro-1H-3-benzazepine
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 2: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme |
N-(2-phenylethyl)-N-(2-phenylsulfinylethyl)formamide
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 2: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 3: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme |
1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With borane-THF |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2: triethylamine / dichloromethane / 0.5 h / 0 °C 3: ammonia / acetonitrile / 1 h / 100 °C / 2068.65 Torr / Autoclave View Scheme | |
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / Reflux 2: triethylamine / dichloromethane / 0.5 h / 20 °C 3: ammonia / 3 h / 90 °C / Sealed tube View Scheme |
2,2’-(1,2-phenylene)diethanol
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 0 °C 2: ammonia / acetonitrile / 1 h / 100 °C / 2068.65 Torr / Autoclave View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 20 °C 2: ammonia / 3 h / 90 °C / Sealed tube View Scheme |
2,3,4,5-tetrahydro-1H-3-benzazepine
trifluoroacetic anhydride
3-trifluoroacetyl-2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 1h; | 100% |
In dichloromethane at -20 - 20℃; for 12h; | 98% |
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 97% |
2,3,4,5-tetrahydro-1H-3-benzazepine
4-Chlorophenyl isothiocyanate
N-(4-Chlorophenyl)-1 ,2,4,5-tetrahydro-3H-3-benzazepine-3-carbothioamide
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; | 100% |
2,3,4,5-tetrahydro-1H-3-benzazepine
1-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone
Conditions | Yield |
---|---|
With acetic anhydride; triethylamine In dichloromethane; water | 95% |
2,3,4,5-tetrahydro-1H-3-benzazepine
acetic anhydride
1-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 18h; | 95% |
With triethylamine In dichloromethane | 50% |
With triethylamine In dichloromethane at 20℃; for 18h; |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid; trifluoroacetic acid at 0℃; regioselective reaction; | 90% |
With sulfuric acid; nitric acid; trifluoroacetic acid at 0℃; for 2h; | 63% |
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine With sulfuric acid at 0℃; for 0.5h; Stage #2: With nitric acid In water at 0℃; for 2h; | 25% |
2,3,4,5-tetrahydro-1H-3-benzazepine
7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine monosulfate
Conditions | Yield |
---|---|
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine With trifluoroacetic acid for 0.5h; Inert atmosphere; Stage #2: With sulfuric acid for 0.25h; Stage #3: With nitric acid at 5 - 10℃; for 4h; regioselective reaction; | 90% |
With sulfuric acid; nitric acid; trifluoroacetic acid at 0 - 10℃; | 86% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation; | 89% |
In isopropyl alcohol for 2h; | 83% |
2,3,4,5-tetrahydro-1H-3-benzazepine
N-[6-chloro-2-(2-pyridinyl)-4-pyrimidinyl]-β-alanine
(3-((2-pyridin-2-yl)-6-(1,2,4,5-tetrahydro-3H-benzo[d]azepin-3-yl)pyrimidin-4-yl)amino)propanoic acid
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 150℃; for 1h; Microwave irradiation; | 86% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation; | 85% |
In isopropyl alcohol for 2h; | 35% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation; | 85% |
In isopropyl alcohol for 2h; | 75% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
In isopropyl alcohol for 2h; | 84% |
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation; | 84% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 25℃; for 2h; Inert atmosphere; | 83% |
2,3,4,5-tetrahydro-1H-3-benzazepine
2-(chloromethyl)-5-nitro-1H-benzo[d]imidazole
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile at 23℃; | 82% |
2,3,4,5-tetrahydro-1H-3-benzazepine
acetyl chloride
1-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 1h; | 80% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
In isopropyl alcohol for 2h; | 80% |
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation; | 80% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation; | 80% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 5℃; for 0.166667h; | 71% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 85℃; for 4h; | 71% |
2,3,4,5-tetrahydro-1H-3-benzazepine
7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitrate salt
Conditions | Yield |
---|---|
With nitric acid at -10℃; for 0.5h; Cooling with acetone-dry ice; | 70% |
2,3,4,5-tetrahydro-1H-3-benzazepine
C20H25N3O4S2
Conditions | Yield |
---|---|
With bis(chlorosulfonyl)amine; triethylamine In dichloromethane; acetonitrile at 25℃; for 12h; | 67% |
Conditions | Yield |
---|---|
In neat (no solvent) at 60℃; for 2h; Mannich Aminomethylation; Autoclave; Microwave irradiation; | 67% |
2,3,4,5-tetrahydro-1H-3-benzazepine
1,1-dimethylethyl[trans-4-(2-oxoethyl)cyclohexyl]carbamate
Conditions | Yield |
---|---|
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine; 1,1-dimethylethyl[trans-4-(2-oxoethyl)cyclohexyl]carbamate With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 0.5h; Stage #2: With water; potassium carbonate In dichloromethane; 1,2-dichloro-ethane | 62% |
2,3,4,5-tetrahydro-1H-3-benzazepine
ethyl N-(2-{4-[2-(1,3-dioxolan-2-yl)ethyl]-2-pyridinyl}-6-{[(4-methylphenyl)sulfonyl]oxy}-4-pyrimidinyl)-β-alaninate
ethyl N-[2-{4-[2-(1,3-dioxolan-2-yl)ethyl]-2-pyridinyl}-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-4-pyrimidinyl]-β-alaninate
Conditions | Yield |
---|---|
In isopropyl alcohol at 150℃; for 1h; Microwave irradiation; | 60% |
2,3,4,5-tetrahydro-1H-3-benzazepine
4-chloro-1-(4-chlorophenyl)butan-1-one
Conditions | Yield |
---|---|
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine; 4-chloro-1-(4-chlorophenyl)butan-1-one With potassium carbonate; potassium iodide In 1,2-dimethoxyethane at 120℃; for 1h; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In diethyl ether Solvent; | 59% |
Conditions | Yield |
---|---|
In neat (no solvent) at 55℃; for 1.5h; Mannich Aminomethylation; Autoclave; Microwave irradiation; | 55% |
2,3,4,5-tetrahydro-1H-3-benzazepine
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide for 1h; | 51.9% |
The 1H-3-Benzazepine, 2, 3, 4, 5-tetrahydro-, with the CAS registry number of 4424-20-8, is also known as 2, 3, 4, 5-Tetrahydro-1H-benzo[d]azepine. This chemical's molecular formula is C10H13N and molecular weight is 147.22. What's more, its IUPAC name is 2, 3, 4, 5-Tetrahydro-1H-3-benzazepine.
Physical properties about 1H-3-Benzazepine, 2, 3, 4, 5-tetrahydro- are: (1)ACD/LogP: 1.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.29; (4)ACD/LogD (pH 7.4): -0.87; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 3.24 Å2; (13)Index of Refraction: 1.53; (14)Molar Refractivity: 46.38 cm3; (15)Molar Volume: 150 cm3; (16)Surface Tension: 35.5 dyne/cm; (17)Density: 0.981 g/cm3; (18)Flash Point: 114.9 °C; (19)Enthalpy of Vaporization: 49.64 kJ/mol; (20)Boiling Point: 258.8 °C at 760 mmHg; (21)Vapour Pressure: 0.0135 mmHg at 25 °C.
Preparation: this chemical is prepared by 3, 4-Dihydro-2H-naphthalen-1-one oxime. The reaction needs reagent Diisobutyl aluminium hydride and solvent CH2Cl2. The reaction time is 1 hours with reaction temperature of 0 °C. The yield is about 92 %.
Uses: it is used to produce other chemicals. For example, it is used to produce 1-Methyl-2, 3, 4, 5-tetrahydro-1H-benzo[b]azepine. This reaction needs reagent n-Butyllithium. Meanwhile, it needs solvents Tetrahydrofuran and Hexane. Other conditions of this reaction are 1.)THF, Hexane, 0 °C; 2.)12 h, r.t..The yield is about 60 %.
You can still convert the following datas into molecular structure:
(1) SMILES: c1cc2c(cc1)CCNCC2
(2) InChI: InChI=1/C10H13N/c1-2-4-10-6-8-11-7-5-9(10)3-1/h1-4,11H,5-8H2
(3) InChIKey: MWVMYAWMFTVYED-UHFFFAOYAW
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