1,4-Diazacycloheptane
di-tert-butyl dicarbonate
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
In dichloromethane at 0℃; for 2h; | 98% |
In acetic acid at 20℃; for 24h; | 90% |
In dichloromethane at 0℃; | 88% |
1,4-Diazacycloheptane
N-(tert-butyloxycarbonyl) azide
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
In ethanol; di-isopropyl ether; water at 15℃; for 4h; | 68.9% |
1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane
1-t-Butoxycarbonylpiperazine
B
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
In methanol; ethyl acetate | A n/a B 38.8% |
2-bromo-pyridine
1-(2-pyridinyl)-1,4-diazepane
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
at 150℃; for 12h; |
1,4-Diazacycloheptane
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With di-tert-butyl dicarbonate at 50℃; |
1-(4'-Cyanomethylphenoxy)-2,3-epoxypropane
1-t-Butoxycarbonylpiperazine
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
In methanol; ethyl acetate |
1,4-Diazacycloheptane
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane |
tert-butyl 1,4-diazepine-1-carboxylate
N-Benzyloxycarbonyl-L-proline
4-(1-benzyloxycarbonyl-pyrrolidine-2-carbonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane | 100% |
cyclobutanone
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: cyclobutanone; tert-butyl 1,4-diazepine-1-carboxylate In 2-methyltetrahydrofuran for 1h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 2-methyltetrahydrofuran for 26h; Inert atmosphere; | 100% |
Stage #1: cyclobutanone; tert-butyl 1,4-diazepine-1-carboxylate In 1,1-dichloroethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In 1,1-dichloroethane for 49h; Stage #3: With sodium hydroxide; water In 1,1-dichloroethane for 1h; | 98% |
Stage #1: cyclobutanone; tert-butyl 1,4-diazepine-1-carboxylate With acetic acid In 1,2-dichloro-ethane at 20 - 25℃; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20 - 25℃; Stage #3: With sodium hydrogencarbonate In water; 1,2-dichloro-ethane at 20 - 25℃; | 96% |
acetone
tert-butyl 1,4-diazepine-1-carboxylate
tert-butyl 4-isopropyl-1,4-diazepane-1-carboxylate
Conditions | Yield |
---|---|
With hydrogen; 1% Pd/C In methanol Molecular sieve; | 100% |
Stage #1: acetone; tert-butyl 1,4-diazepine-1-carboxylate In methanol for 0.0833333h; Inert atmosphere; Molecular sieve; Stage #2: With hydrogenchloride; sodium cyanoborohydride In methanol for 20h; Inert atmosphere; | 93% |
Stage #1: acetone; tert-butyl 1,4-diazepine-1-carboxylate In methanol at 0℃; for 0.333333h; Stage #2: With sodium cyanoborohydride In methanol at 0 - 20℃; for 56.3333h; |
bromochlorobenzene
tert-butyl 1,4-diazepine-1-carboxylate
tert-butyl 4-(4-chlorophenyl)-1,4-diazepane-1-carboxylate
Conditions | Yield |
---|---|
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 23h; Heating / reflux; | 100% |
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 23h; Heating / reflux; | 100% |
tert-butyl 1,4-diazepine-1-carboxylate
2-chloro-4,6-dimethoxy-5-nitro-pyrimidine
4-(4,6-dimethoxy-5-nitro-pyrimidin-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With triethylamine In ethanol at 0 - 20℃; | 100% |
5-chloro-3-methyl-1,2,4-thiazole
tert-butyl 1,4-diazepine-1-carboxylate
tert-butyl 4-(3-methyl-1,2,4-thiadiazol-5-yl)-1,4-diazepane-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In ethanol for 2h; Heating; | 100% |
3-amino-5-tert-butylisoxazole
bis(trichloromethyl) carbonate
tert-butyl 1,4-diazepine-1-carboxylate
4-(5-tert-butyl-isoxazol-3-ylcarbamoyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 100% |
Stage #1: 3-amino-5-tert-butylisoxazole; bis(trichloromethyl) carbonate With N-ethyl-N,N-diisopropylamine In dichloromethane for 2.5h; Stage #2: tert-butyl 1,4-diazepine-1-carboxylate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; | 58% |
Stage #1: 3-amino-5-tert-butylisoxazole; bis(trichloromethyl) carbonate With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.0833333 - 2.5h; Stage #2: tert-butyl 1,4-diazepine-1-carboxylate With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; Product distribution / selectivity; |
isoquinoline-5-sulfonyl chloride hydrochloride
tert-butyl 1,4-diazepine-1-carboxylate
4-(isoquinoline-5-sulfonyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 3h; | 100% |
iodobenzene
tert-butyl 1,4-diazepine-1-carboxylate
4-phenyl-1,4-diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos In 1,4-dioxane; tert-butyl alcohol for 2h; Inert atmosphere; Reflux; | 100% |
6-[1-(6-fluoro-2-pyridyl)pyrazolo[4,3-c]pyridin-6-yl]-N-[(4-methoxyphenyl)methyl]pyrazin-2-amine
tert-butyl 1,4-diazepine-1-carboxylate
tert-butyl 4-[6-[6-[6-[(4-methoxyphenyl)methylamino]pyrazin-2-yl]pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-1,4-diazepane-1-carboxylate
Conditions | Yield |
---|---|
With 4-methyl-morpholine In 1-methyl-pyrrolidin-2-one at 110℃; Sealed tube; | 100% |
tert-butyl 1,4-diazepine-1-carboxylate
N,N-Dimethylcarbamoyl chloride
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 2h; | 100% |
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With potassium fluoride In dimethyl sulfoxide at 100℃; for 144h; Sealed tube; | 100% |
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With potassium phosphate In 1-methyl-pyrrolidin-2-one at 25 - 90℃; for 16h; | 100% |
1-bromo-4-butene
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In tetrahydrofuran Reflux; | 100% |
2-chloro-4-fluorobenzonitrile
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; | 100% |
2-chloro-1-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
tert-butyl 1,4-diazepine-1-carboxylate
4-(3-formyl-1-phenyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
In 1,4-dioxane at 110℃; for 19.5h; Heating / reflux; | 99.5% |
bromobenzene
tert-butyl 1,4-diazepine-1-carboxylate
4-phenyl-1,4-diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; XPhos In toluene; tert-butyl alcohol at 120℃; Buchwald-Hartwig reaction; Inert atmosphere; | 99% |
With palladium diacetate; sodium t-butanolate; XPhos In toluene; tert-butyl alcohol for 24h; Buchwald-Hartwig Coupling; Reflux; |
para-bromotoluene
tert-butyl 1,4-diazepine-1-carboxylate
4-(4-methylphenyl)-1,4-diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; XPhos In toluene; tert-butyl alcohol at 160℃; for 0.166667h; Buchwald-Hartwig reaction; Inert atmosphere; Microwave irradiation; | 99% |
With tri-tert-butyl phosphine; α,α,α-trifluorotoluene; palladium diacetate; 2,4,6-tri(tert-butyl)phenol sodium salt In toluene at 100℃; for 1h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; Microwave irradiation; | 89% |
3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile; tert-butyl 1,4-diazepine-1-carboxylate With acetic acid In dichloromethane for 1h; Reflux; Stage #2: With sodium cyanoborohydride In ethanol; dichloromethane at 20℃; for 17h; | 99% |
Ethyl isothiocyanate
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; | 99% |
(1aS,6aR)-3,5-dichloro-6,6a-di-hydro-1aH-1-oxa-cyclopropa[a]indene
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
In acetonitrile at 80℃; regioselective reaction; | 99% |
2-benzofuroyl chloride
tert-butyl 1,4-diazepine-1-carboxylate
tert-butyl 4-(benzofuran-2-carbonyl)-homopiperazine-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; | 99% |
1-bromo-4-methoxy-benzene
tert-butyl 1,4-diazepine-1-carboxylate
4-(4-methoxyphenyl)-1,4-diazepane-1-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With palladium diacetate; sodium t-butanolate; XPhos In toluene; tert-butyl alcohol at 120℃; for 10h; Buchwald-Hartwig reaction; Inert atmosphere; | 98% |
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; tris-(o-tolyl)phosphine In toluene at 100℃; for 18h; |
4-methoxy-phenyl-sulphonyl chloride
tert-butyl 1,4-diazepine-1-carboxylate
C17H26N2O5S
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane | 98% |
1-(2-(5-bromopentyloxy)-3,5-dibromophenoxy)-2,4-dibromobenzene
tert-butyl 1,4-diazepine-1-carboxylate
tert-butyl 4-(5-(2-(2, 4-Dibromophenoxy)-4,6-dibromophenoxy)pentyl)-1,4-diazepane-1-carboxylate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 6h; Inert atmosphere; Reflux; | 98% |
cyclopropanecarboxylic acid chloride
tert-butyl 1,4-diazepine-1-carboxylate
cyclopropyl(1,4-N-cycloheptyl-1-yl)methanone hydrochloride
Conditions | Yield |
---|---|
Stage #1: cyclopropanecarboxylic acid chloride; tert-butyl 1,4-diazepine-1-carboxylate With triethylamine In dichloromethane for 1.66667h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; dichloromethane at 20 - 40℃; for 41h; | 98% |
methyl thioisocyanate
tert-butyl 1,4-diazepine-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 20℃; | 98% |
tert-butyl 1,4-diazepine-1-carboxylate
cyclopropanecarboxylic acid
tert-butyl 4-(cyclopropylaminocarbamoyl)-1,4-N-cycloheptane-1-carboxylate
Conditions | Yield |
---|---|
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere; | 98% |
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 10h; | 98% |
2-Thiophenecarbonyl chloride
tert-butyl 1,4-diazepine-1-carboxylate
tert-butyl 4-(thiophene-2-carbonyl)-1,4-diazepane-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; | 98% |
The 1-Boc-homopiperazine with CAS registry number of 112275-50-0 is also known as 1,1-Dimethylethyl1,4-diazepane-1-carboxylate. The IUPAC name is tert-Butyl 1,4-diazepane-1-carboxylate. It belongs to product categories of Piperidines, Piperidones, Piperazines; Heterocycles Series; Piperaizine; API Intermediates. In addition, the formula is C10H20N2O2 and the molecular weight is 200.28. This chemical should be sealed in cool, dry place away from oxidants and carbon dioxide with protection of inert gas.
Physical properties about 1-Boc-homopiperazine are: (1)ACD/LogP: 0.94; (2)ACD/LogD (pH 5.5): -2.11; (3)ACD/LogD (pH 7.4): -1.16; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.464; (12)Molar Refractivity: 54.78 cm3; (13)Molar Volume: 198.4 cm3; (14)Surface Tension: 33.4 dyne/cm; (15)Density: 1.009 g/cm3; (16)Flash Point: 121.9 °C; (17)Enthalpy of Vaporization: 51.65 kJ/mol; (18)Boiling Point: 277.9 °C at 760 mmHg; (19)Vapour Pressure: 0.0044 mmHg at 25 °C.
Uses of 1-Boc-homopiperazine: it is used to produce 4-(7,8,9,10-tetrahydro-6H-cyclohepta[b]quinolin-11-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester by reaction with 11-bromo-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinoline. The reaction occurs with reagents Cu, I2 at the temperature of 180 °C for 18 hours. The yield is about 44%.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(C)(C)OC(=O)N1CCCNCC1
2. InChI: InChI=1S/C10H20N2O2/c1-10(2,3)14-9(13)12-7-4-5-11-6-8-12/h11H,4-8H2,1-3H3
3. InChIKey: WDPWEXWMQDRXAL-UHFFFAOYSA-N
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