Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol | 100% |
With sodium tetrahydroborate In ethanol | 95% |
With sodium tetrahydroborate In methanol; dichloromethane | 88% |
N,N'-dibenzoyl-N,N'-dibenzylethylenediamine
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 0.666667h; Heating; | 94% |
1,2-dibenzyl-1,2-diazetin-3-one
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
With B2H6-THF for 2h; Heating; | 85% |
With diborane In tetrahydrofuran |
Conditions | Yield |
---|---|
Stage #1: benzaldehyde; ethylenediamine With sodium sulfate; triethylamine In ethyl acetate at 20℃; for 14h; Stage #2: With sodium tetrahydroborate In methanol; ethyl acetate for 6h; | 70% |
Stage #1: benzaldehyde; ethylenediamine Stage #2: With sodium tetrahydroborate | 69% |
With sodium tetrahydroborate In methanol at 20℃; Reflux; | 67.6% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating; | 51% |
formic acid
N,N'-bis(benzyliden)ethylendiamine
sodium formate
A
N,N'-Dibenzylethylenediamine
B
N-benzylethylenediamine
N,N'-bis(benzyliden)ethylendiamine
A
N,N'-Dibenzylethylenediamine
B
N-benzylethylenediamine
Conditions | Yield |
---|---|
With formic acid |
1,2-bis-(benzenesulfonyl-benzyl-amino)-ethane
A
N,N'-Dibenzylethylenediamine
B
N-benzylethylenediamine
Conditions | Yield |
---|---|
With hydrogenchloride at 170 - 180℃; im geschlossenen Rohr; |
formic acid
N-(2-formylaminoethyl)formamide
benzaldehyde
A
N,N'-Dibenzylethylenediamine
B
N-benzylethylenediamine
Conditions | Yield |
---|---|
auch unter Zusatz von Natriumformiat und Kaliumformiat; |
N-(2-formylaminoethyl)formamide
benzaldehyde
A
N,N'-Dibenzylethylenediamine
B
N-benzylethylenediamine
Conditions | Yield |
---|---|
With formic acid |
benzaldehyde
ethylenediamine
A
N,N'-Dibenzylethylenediamine
B
N-benzylethylenediamine
Conditions | Yield |
---|---|
With ethanol; sodium | |
With methanol; nickel at 80 - 100℃; under 58840.6 Torr; Hydrogenation; |
N,N'-bis(benzyliden)ethylendiamine
benzyl chloride
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
With hexan-1-ol auch mit anderen Schiffschen Basen des Aethylendiamins; |
N,N'-dibenzyl-N,N'-1,2-ethanediylbisformamide
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol Heating; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 16h; Heating; |
N,N'-bis(benzyliden)ethylendiamine
benzaldehyde
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 0℃; for 3h; Yield given; |
benzaldehyde
ethylenediamine
A
1,3-dibenzyl-2-phenylimidazolidine
B
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 0℃; under 760 Torr; for 20h; |
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 1h; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / pyridine / benzene / 0.5 h / 60 - 70 °C 2: 95 percent / aq. NaOH / methanol / 1 h / 0 °C 3: 86 percent / methanol / 35 - 40 °C / Electrolysis 4: 94 percent / HCl / ethanol / 0.67 h / Heating View Scheme |
[benzoyl(benzyl)amino]acetic acid
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / methanol / 35 - 40 °C / Electrolysis 2: 94 percent / HCl / ethanol / 0.67 h / Heating View Scheme |
ethyl N-[benzoyl(benzyl)amino]acetate
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 95 percent / aq. NaOH / methanol / 1 h / 0 °C 2: 86 percent / methanol / 35 - 40 °C / Electrolysis 3: 94 percent / HCl / ethanol / 0.67 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 92 percent / triethylamine / CH2Cl2 / 2 h / 20 °C 2: 89 percent / pyridine / benzene / 0.5 h / 60 - 70 °C 3: 95 percent / aq. NaOH / methanol / 1 h / 0 °C 4: 86 percent / methanol / 35 - 40 °C / Electrolysis 5: 94 percent / HCl / ethanol / 0.67 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanol / 4 h / 20 °C 2: NaBH4 / methanol / 1 h / 20 °C View Scheme |
1,2-dibenzylpyrazolidine-3,5-dione
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: TosN3, NEt3 / acetonitrile 2: 50 percent / H2O / diethyl ether / Irradiation 3: benzene / Heating 4: diborane / tetrahydrofuran View Scheme | |
Multi-step reaction with 4 steps 1: 66 percent / triethylamine, toluene-p-sulphonyl azide / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, 2 h 2: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation 3: 80 percent / toluene / 2 h / Heating 4: 85 percent / diborane-THF complex / 2 h / Heating View Scheme |
1,2-dibenzyl-3-oxo-1,2-diazetidine-4-carboxylic acid
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: benzene / Heating 2: diborane / tetrahydrofuran View Scheme | |
Multi-step reaction with 2 steps 1: 80 percent / toluene / 2 h / Heating 2: 85 percent / diborane-THF complex / 2 h / Heating View Scheme |
4-diazo-1,2-dibenzylpyrazolidine-3,5-dione
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 50 percent / H2O / diethyl ether / Irradiation 2: benzene / Heating 3: diborane / tetrahydrofuran View Scheme | |
Multi-step reaction with 3 steps 1: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation 2: 80 percent / toluene / 2 h / Heating 3: 85 percent / diborane-THF complex / 2 h / Heating View Scheme |
ethyl 3-benzylidenecarbazate
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 95 percent / 40 aq. percent NaOH, trimethylbenzylammonium chloride / benzene / 17 h / Heating 2: 75 percent / H2 / 10 percent Pd-C / ethanol 3: 72 percent / triethylamine / benzene / 3 h 4: NaOEt / ethanol / 20 h / Heating 5: H2O; acetonitrile / 2 h / Heating 6: 66 percent / triethylamine, toluene-p-sulphonyl azide / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, 2 h 7: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation 8: 80 percent / toluene / 2 h / Heating 9: 85 percent / diborane-THF complex / 2 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 95 percent / 40 aq. percent NaOH, trimethylbenzylammonium chloride / benzene / 17 h / Heating 2: 75 percent / H2 / 10 percent Pd-C / ethanol 3: 72 percent / triethylamine / benzene / 3 h 4: NaOEt / ethanol / 20 h / Heating 5: H2O; acetonitrile / 2 h / Heating 6: 66 percent / triethylamine, toluene-p-sulphonyl azide / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, 2 h 7: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation 8: 80 percent / toluene / 2 h / Heating 9: 85 percent / diborane-THF complex / 2 h / Heating View Scheme |
2,3-dibromopropionic acid ethyl ester
N,N'-Dibenzylethylenediamine
ethyl 1,4-dibenzylpiperazin-2-carboxylate
Conditions | Yield |
---|---|
With triethylamine In toluene at 40 - 80℃; for 3h; | 100% |
With triethylamine In toluene at 80 - 95℃; for 3h; | 94% |
With triethylamine In toluene at 80℃; for 3h; | 93% |
Conditions | Yield |
---|---|
In water; isopropyl alcohol for 1h; aza-Michael addition; Heating; | 100% |
bromoacetic acid tert-butyl ester
N,N'-Dibenzylethylenediamine
N,N'-(benzyl)-N,N'-[(tert-butoxycarbonyl)methyl]ethylenediamine
Conditions | Yield |
---|---|
Stage #1: N,N'-Dibenzylethylenediamine With potassium carbonate In acetonitrile for 1h; Reflux; Stage #2: bromoacetic acid tert-butyl ester In acetonitrile for 24h; Reflux; | 100% |
With potassium carbonate In acetonitrile for 24h; Reflux; | 100% |
Stage #1: N,N'-Dibenzylethylenediamine With sodium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In acetonitrile at 90℃; | 95% |
With sodium carbonate In acetonitrile at 60℃; | 93% |
pyridine-2-carbaldehyde
N,N'-Dibenzylethylenediamine
2-(1,3-dibenzyl-imidazolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
In water at 20℃; for 3h; | 99% |
thiophene-2-carbaldehyde
N,N'-Dibenzylethylenediamine
1,3-dibenzyl-2-thiophen-2-yl-imidazolidine
Conditions | Yield |
---|---|
In water at 20℃; for 3h; | 99% |
In ethanol; water at 80℃; for 3h; | 50% |
In ethanol; water at 20℃; | 50% |
N,N'-Dibenzylethylenediamine
N,N'-Dibenzyl-N,N'-dinitroso-1,2-diaminoethane
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite for 20h; Heating; | 98% |
With hydrogenchloride; sodium nitrite In water | 94% |
O,O'-di(α-bromo-α-phenylacetyl)-L-tartaric acid diisopropyl ester
N,N'-Dibenzylethylenediamine
A
(S)-1,4-dibenzyl-3-phenylpiperazin-2-one
B
(R)-1,4-dibenzyl-3-phenylpiperazin-2-one
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; enantioselective reaction; | A 98% B n/a |
3-methylbenzene-1,2-diol
N,N'-Dibenzylethylenediamine
1,4-dibenzyl-5-methyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione
Conditions | Yield |
---|---|
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction; | 98% |
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction; | 93.2% |
Conditions | Yield |
---|---|
With C14H38BaSi4*3C4H8O In benzene at 60℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 98% |
benzaldehyde
N,N'-Dibenzylethylenediamine
1,3-dibenzyl-2-phenylimidazolidine
Conditions | Yield |
---|---|
In water for 3h; | 97% |
In water at 20℃; for 3h; | 91% |
In benzene | 85% |
Conditions | Yield |
---|---|
Stage #1: N,N'-Dibenzylethylenediamine; 1-bromo-3-propanol With N-ethyl-N,N-diisopropylamine In acetonitrile for 12h; Heating; Stage #2: trifluoroacetic acid In water; acetonitrile | 97% |
acetic acid
N,N'-Dibenzylethylenediamine
N,N'-dibenzylethylenediamine diacetate
Conditions | Yield |
---|---|
In ethyl acetate at 5 - 60℃; for 1h; | 96.91% |
2-chloro-benzaldehyde
N,N'-Dibenzylethylenediamine
1,3-dibenzyl-2-(2-chloro-phenyl)-imidazolidine
Conditions | Yield |
---|---|
In water at 20℃; for 3h; | 96% |
1,4-dioxane-2,6-dione
N,N'-Dibenzylethylenediamine
[(Benzyl-{2-[benzyl-(2-carboxymethoxy-acetyl)-amino]-ethyl}-carbamoyl)-methoxy]-acetic acid
Conditions | Yield |
---|---|
In benzene | 96% |
In tetrahydrofuran at 50℃; for 12h; | 96% |
With triethylamine In benzene for 4h; Heating; |
formaldehyd
2,4-di-tert-Butylphenol
N,N'-Dibenzylethylenediamine
N,N'-dibenzyl-N,N'-bis[(3,5-di-t-butyl-2-hydroxyphenyl)methylene]-1,2-diaminoethane
Conditions | Yield |
---|---|
In methanol Mannich condensation; Heating; | 96% |
In methanol; water Reflux; | 90.1% |
In ethanol at 90℃; | 25% |
In water Mannich reaction; |
2,4-dichlorobenzaldeyhde
N,N'-Dibenzylethylenediamine
1,3-dibenzyl-2-(2,4-dichloro-phenyl)-imidazolidine
Conditions | Yield |
---|---|
In water at 80℃; for 3h; | 96% |
cis-1,4-bis(acetyloxy)but-2-ene
N,N'-Dibenzylethylenediamine
racemic-1,4-Dibenzyl-2-vinylpiperazine
Conditions | Yield |
---|---|
Stage #1: cis-1,4-bis(acetyloxy)but-2-ene; N,N'-Dibenzylethylenediamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triisopropyl phosphite In tetrahydrofuran for 18.25h; Stage #2: With sodium hydroxide In diethyl ether; water pH=14; | 96% |
With triphenylphosphine; dichloro bis(acetonitrile) palladium(II) In benzene Heating; | 67% |
Stage #1: cis-1,4-bis(acetyloxy)but-2-ene; N,N'-Dibenzylethylenediamine In tetrahydrofuran for 18.25h; Stage #2: With sodium hydroxide In diethyl ether; water pH=14; |
formaldehyd
Nitroethane
N,N'-Dibenzylethylenediamine
1,4-dibenzyl-6-methyl-6-nitroperhydro-1,4-diazepine
Conditions | Yield |
---|---|
Stage #1: formaldehyd; N,N'-Dibenzylethylenediamine In ethanol for 4h; Reflux; Stage #2: Nitroethane In ethanol for 16h; Inert atmosphere; Reflux; | 96% |
Stage #1: formaldehyd; N,N'-Dibenzylethylenediamine In ethanol for 2h; Reflux; Inert atmosphere; Stage #2: Nitroethane In ethanol Reflux; Inert atmosphere; | 78% |
3,4-Dihydroxybenzoic acid
N,N'-Dibenzylethylenediamine
1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione
Conditions | Yield |
---|---|
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction; | 95.5% |
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction; |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 95% |
In N,N-dimethyl-formamide at 20℃; for 12h; | 84.7% |
benzene-1,2-diol
N,N'-Dibenzylethylenediamine
1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione
Conditions | Yield |
---|---|
In aq. phosphate buffer at 20℃; pH=7; Mechanism; pH-value; Electrochemical reaction; | 94.8% |
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction; |
Conditions | Yield |
---|---|
In water at 25℃; Electrochemical reaction; Green chemistry; | 94.3% |
Conditions | Yield |
---|---|
In water at 20℃; for 3h; | 94% |
(E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
94% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; N,N'-Dibenzylethylenediamine In methanol at 20℃; for 0.333333h; Stage #2: β-naphthol In methanol for 2h; | 93% |
N,N'-Dibenzylethylenediamine
Conditions | Yield |
---|---|
In benzene at 50℃; for 5h; Molecular sieve; | 93% |
In benzene at 50℃; for 5h; Molecular sieve; | 93% |
3-methocycatechol
N,N'-Dibenzylethylenediamine
1,4-dibenzyl-5-methoxy-1,2,3,4-tetrahydroquinoxaline-6,7-dione
Conditions | Yield |
---|---|
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction; | 92.6% |
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction; | 66% |
perfluorobenzaldehyde
N,N'-Dibenzylethylenediamine
1,3-dibenzyl-2-pentafluorophenyl-imidazolidine
Conditions | Yield |
---|---|
In water at 20℃; for 3h; | 92% |
1. | orl-mus LD50:388 mg/kg | CNCRA6 Cancer Chemotherapy Reports. 52 (1968),579. | ||
2. | ipr-mus LD50:50 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . | ||
3. | par-mus LD50:80 mg/kg | ANTCAO Antibiotics and Chemotherapy. 4 (1954),633. |
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