cyclohexanone
dimethyl amine
A
N-methylcyclohexylamine
B
N,N-dimethyl-cyclohexanamine
C
cyclohexanol
Conditions | Yield |
---|---|
With hydrogen at 160 - 220℃; under 67506.8 - 97509.8 Torr; for 100 - 1000h; Product distribution / selectivity; | A 0.1% B 96% C 0.5% |
With hydrogen at 160 - 180℃; under 63756.4 - 97509.8 Torr; for 100 - 400h; Product distribution / selectivity; | A 0.1% B 94% C 2% |
N-butylamine
A
butyl-(3-methyl-3H-benzothiazol-2-ylidene)-amine
B
N-methylcyclohexylamine
Conditions | Yield |
---|---|
at 25℃; for 3h; | A 95% B 83% |
In dichloromethane at 25℃; for 3h; | A 95% B 83% |
Conditions | Yield |
---|---|
With Zr12(μ3-O)5[(μ3-O)CoCl]8[(μ2-O)2(μ3-O)CoCl]3Li3(triphenyldicarboxylate)9; hydrogen In toluene at 110℃; under 30003 Torr; for 42h; Catalytic behavior; Inert atmosphere; Schlenk technique; | 92% |
With dimethyl sulfoxide In water at 100℃; Green chemistry; | 65% |
Conditions | Yield |
---|---|
With hydrogen In neat (no solvent) at 80℃; under 7600.51 Torr; for 24h; Catalytic behavior; Autoclave; | 91% |
With dichloro(μ-chloro)(μ-hydrido)bis(η-p-cymene)diruthenium(II); hydrogen In neat (no solvent) at 75℃; under 37503.8 Torr; for 24h; | 80% |
With lithium; methylamine |
Conditions | Yield |
---|---|
With iridium bromide; zinc In 1,4-dioxane; water at 30℃; for 72h; | 85% |
With titanium(IV) isopropylate; sodium tetrahydroborate; triethylamine 1.) EtOH, 25 deg C, 10 h, 2.) EtOH, 25 deg C, 8 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride; Zr(BH4)2Cl2(dabco)2 In methanol for 1h; Heating; | 78% |
With D-glucose; glucose dehydrogenase CDX-901; imine reductase 48 from Rhizobium sullae; nicotinamide adenine dinucleotide phosphate In aq. buffer at 25℃; for 24h; pH=9; Enzymatic reaction; | 66% |
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran; methanol Flow reactor; chemoselective reaction; | 37% |
Conditions | Yield |
---|---|
With rhodium(III) chloride hydrate; potassium tert-butylate at 130℃; for 48h; Sealed tube; High pressure; | 75% |
With thorium dioxide at 320℃; | |
rhodium hydrido (PEt3)3 complex for 10h; | 99 % Chromat. |
With platinum on carbon; hydrogen; sodium hydroxide at 130℃; under 30003 Torr; for 36h; Autoclave; | 74 %Chromat. |
With palladium 10% on activated carbon; potassium tert-butylate at 130℃; for 12h; |
N-(6-Methoxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-N-methyl-hydroxylamine
N-methylcyclohexylamine
Conditions | Yield |
---|---|
With carbon disulfide In acetonitrile for 1.5h; Ambient temperature; | 71% |
Conditions | Yield |
---|---|
Stage #1: chloromethyltriethoxysilane; cyclohexylamine at 87℃; for 18h; Stage #2: With water In ethanol for 48h; Heating; Further stages.; | 68% |
N-methylcyclohexylamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether -60 degC -> room temp.; | 67% |
N-(benzenesulfenyl)-N-methylcyclohexylamine
N-methylcyclohexylamine
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In cyclohexane Heating; | 53% |
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In cyclohexane for 0.25h; Mechanism; Product distribution; Heating; other conditions: other solvent, no reagents and catalysts; other sulpenamides as starting material; Competitive reaction of C-SPh compound 11 with Bu3nH: comparison of the reactivities of N-SPh and C-SPh bonds; |
cyclohexanone
methylamine
A
N-methylcyclohexylamine
B
cyclohexanol
Conditions | Yield |
---|---|
With hydrogenchloride; sodium tetrahydroborate In isopropyl alcohol at 20 - 30℃; | A 45% B 40% |
With potassium hydroxide; potassium phosphate In water at 18 - 20℃; pH 12, electrochemical reaction; |
cyclohexylamine
carbonic acid dimethyl ester
A
N-methylcyclohexylamine
B
N,N-dimethyl-cyclohexanamine
Conditions | Yield |
---|---|
With binder-free NaY zeolite Heating; | A 5% B n/a |
diazomethane
cyclohexylamine
A
N-methylcyclohexylamine
B
N,N-dimethyl-cyclohexanamine
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate |
Conditions | Yield |
---|---|
With sodium hydroxide; potassium hexacyanoferrate(III) | |
With diethyl ether; bromocyane und Erhitzen des hierbei erhaltenen Reaktionsprodukts mit wss. H2SO4; | |
With naphthalene-1,4-dicarbonitrile In methanol; acetonitrile for 0.166667h; UV-irradiation; | 11 % Chromat. |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
N-(cyanomethyl)cyclohexylamine
A
N-methylcyclohexylamine
B
N-cyclohexylethylenediamine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
N-methylaniline hydrochloride
A
N-methylcyclohexylamine
B
N-Methyldicyclohexylamine
Conditions | Yield |
---|---|
With ethanol; platinum at 70℃; under 1520 - 2280 Torr; Hydrogenation; |
4-methylamino-phenol; hydrochloride
A
N-methylcyclohexylamine
B
4-(methylamino)cyclohexanol
Conditions | Yield |
---|---|
With water; platinum under 2280 Torr; Hydrogenation.entsteht ein Gemisch von cis- und trans-Form; |
N-Methylformamide
cyclohexanone
A
N-methylcyclohexylamine
B
N-Methyldicyclohexylamine
Conditions | Yield |
---|---|
With formic acid |
diethyl ether
cyclohexylamine
dimethyl sulfate
A
N-methylcyclohexylamine
B
N,N-dimethyl-cyclohexanamine
Conditions | Yield |
---|---|
With diethyl ether |
N-(α-phenylbenzylidene)cyclohexylamine
methyl iodide
A
benzophenone
B
N-methylcyclohexylamine
Conditions | Yield |
---|---|
anschliessend beim Kochen mit 90prozentigem Alkohol; |
N-chloromethylamine
cyclohexyl-dimethylborane
N-methylcyclohexylamine
Conditions | Yield |
---|---|
a) 0 deg C, 5-10 min, b) RT, 60 min; Yield given; |
Diphenylmethane
lithium cyclohexyl(methyl)amide
A
N-methylcyclohexylamine
B
diphenylmethyllithium
Conditions | Yield |
---|---|
In tetrahydrofuran at 30℃; Equilibrium constant; |
triphenylmethane
lithium cyclohexyl(methyl)amide
A
N-methylcyclohexylamine
B
trityllithium
Conditions | Yield |
---|---|
In tetrahydrofuran at 30℃; Equilibrium constant; |
Conditions | Yield |
---|---|
With hydrogenchloride; zinc |
methanol
cyclohexylamine
A
N-methylcyclohexylamine
B
N,N-dimethyl-cyclohexanamine
Conditions | Yield |
---|---|
ruthenium trichloride; tri-n-butyl phosphite In 1,4-dioxane at 180℃; for 15h; | A 3 % Chromat. B 14 % Chromat. |
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); hydrogen at 120℃; under 30003 Torr; for 24h; Glovebox; | A n/a B 31 %Spectr. |
With C19H37IrN4(2+)*2Cl(1-)*2H2O; potassium carbonate at 50℃; for 17h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; | A 14 %Chromat. B 61 %Chromat. |
With hydrogen at 55℃; under 750.075 Torr; for 24h; Irradiation; Green chemistry; |
Methyltrimethoxyphosphonium tetrafluoroborate
cyclohexylamine
A
N-methylcyclohexylamine
B
N,N-dimethyl-cyclohexanamine
Conditions | Yield |
---|---|
for 12h; Ambient temperature; Yield given. Yields of byproduct given; |
N-methylcyclohexylamine
2-(vinyloxy)ethyl isothiocyanate
1-Cyclohexyl-1-methyl-3-(2-vinyloxy-ethyl)-thiourea
Conditions | Yield |
---|---|
100% |
N-methylcyclohexylamine
2-phenyl-1-(2-thioxothiazolidin-3-yl)ethan-1-one
N-cyclohexyl-N-methyl-2-phenylacetamide
Conditions | Yield |
---|---|
100% | |
In dichloromethane for 0.0333333h; Ambient temperature; | 100% |
N-methylcyclohexylamine
benzenesulfenyl chloride
N-(benzenesulfenyl)-N-methylcyclohexylamine
Conditions | Yield |
---|---|
With triethylamine In diethyl ether for 0.166667h; | 100% |
N-methylcyclohexylamine
bis(trichloromethyl) carbonate
N-methyl-N-cyclohexylaminocarbonyl chloride
Conditions | Yield |
---|---|
With pyridine In toluene | 100% |
With pyridine In toluene | |
With pyridine In dichloromethane at 20℃; for 2h; |
Conditions | Yield |
---|---|
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 100℃; | 100% |
With rhodium(III) chloride hydrate; potassium tert-butylate at 130℃; for 48h; Sealed tube; High pressure; | 45% |
With Ru(OAc)2(1,1′-bis(diisopropylphosphino)ferrocene)(CO); trifluoroacetic acid at 100℃; for 24h; Temperature; Inert atmosphere; Schlenk technique; | |
With palladium 10% on activated carbon; potassium tert-butylate at 130℃; for 14h; |
Conditions | Yield |
---|---|
With trichloroisocyanuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.25h; | 99% |
With sulfuric acid; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.166667h; | 98% |
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; water; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.0666667h; Reagent/catalyst; | 98% |
N-methylcyclohexylamine
1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one
N-cyclohexyl-N-methylhexadecanamide
Conditions | Yield |
---|---|
In dichloromethane for 0.166667h; Ambient temperature; | 99% |
N-methylcyclohexylamine
2-bromobenzoic acid chloride
2-bromo-N-cyclohexyl-N-methylbenzamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 2h; Ambient temperature; | 99% |
With N-ethyl-N,N-diisopropylamine In diethyl ether at 0 - 20℃; Inert atmosphere; | 4.5 g |
N-methylcyclohexylamine
4-chloro-1H-pyrrolo[2,3-d]pyrimidine
N-cyclohexyl-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
Conditions | Yield |
---|---|
In 1,4-dioxane at 110℃; for 9h; Microwave irradiation; Sealed tube; | 99% |
Stage #1: N-methylcyclohexylamine; 4-chloro-1H-pyrrolo[2,3-d]pyrimidine In tert-butyl alcohol at 100℃; for 24h; Stage #2: With hydrogenchloride In water; tert-butyl alcohol pH=1; Stage #3: With sodium hydroxide In water; tert-butyl alcohol pH=14; | 88% |
In tert-butyl alcohol at 85℃; |
2,4,6-trimethyl-pyridine
N-methylcyclohexylamine
sulfuric acid
tetrabutylammomium bromide
Conditions | Yield |
---|---|
In 1,1,2,2-tetrachloroethylene | 99% |
N-methylcyclohexylamine
1-Bromo-2-bromomethyl-benzene
N-(2-bromobenzyl)-N-methylcyclohexylamine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With C50H61Cl2N3Pd; potassium tert-butylate In 1,4-dioxane at 100℃; for 2h; | 99% |
2-chloro-1,3-benzoxazole
N-methylcyclohexylamine
N-cyclohexyl-N-methylbenzo[d]oxazol-2-amine
Conditions | Yield |
---|---|
With C50H61Cl2N3Pd; potassium tert-butylate In 1,4-dioxane at 100℃; for 2h; | 99% |
N-methylcyclohexylamine
zirconium(IV) chloride
tetrakis(cyclohexylmethylamide)zirconium
Conditions | Yield |
---|---|
With Li-n-Bu In hexane; toluene in oxygen and moisture free atmosphere; soln. of ligand in toluene addeddropwise to soln. of Li-n-Bu in hexane; stirred at room temp. for 2.5 h ; ZrCl4 added gradually for 30 min; stirred for 18 h; filtered; filtrate reduced to oil under reduced pressure; elem. anal.; | 98.7% |
Conditions | Yield |
---|---|
In methanol at 50℃; under 6000480 Torr; for 96h; | 98% |
N-methylcyclohexylamine
methyl 2-isothiocyanatobenzoate
methyl 2-(3-cyclohexyl-3-methylthioureido)benzoate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; | 98% |
In dichloromethane at 20℃; |
5-methyl-1,3-benzoxazole
N-methylcyclohexylamine
N-cyclohexyl-N'-(2-hydroxy-5-methylphenyl)-N-methylmethanimidamide
Conditions | Yield |
---|---|
at 80℃; for 12h; | 98% |
In acetonitrile at 80℃; for 10h; |
N-methylcyclohexylamine
2-Iodobenzoyl chloride
N-cyclohexyl-2-iodo-N-methylbenzamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 5h; | 98% |
N-methylcyclohexylamine
1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one
Conditions | Yield |
---|---|
Stage #1: N-methylcyclohexylamine With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-1,2,3,4-tetrahydroquinoline In tetrahydrofuran at -10 - 20℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: 1-tosyl-4-vinyl-1,4-dihydro-2H-benzo[d] [1,3]oxazin-2-one In tetrahydrofuran at -10℃; for 5h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 98% |
N-methylcyclohexylamine
ethyl 4-chloro-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate
Conditions | Yield |
---|---|
In ethanol at 80℃; for 2h; Inert atmosphere; | 98% |
N-methylcyclohexylamine
di-tert-butyl dicarbonate
Conditions | Yield |
---|---|
With saccharin sulfonic acid In hexane at 20℃; for 1h; | 97% |
With piperazine functionalized zirconium-Fe3O4-MCM-41 magnetic nanoparticles In neat (no solvent) at 20℃; for 0.166667h; Time; | 91% |
With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.166667h; Green chemistry; chemoselective reaction; | 90% |
N-methylcyclohexylamine
Propiolic acid
N-cyclohexyl-N-methylpropiolamide
Conditions | Yield |
---|---|
Stage #1: Propiolic acid With pivaloyl chloride; potassium carbonate In tetrahydrofuran for 1h; Inert atmosphere; Cooling; Stage #2: N-methylcyclohexylamine In tetrahydrofuran for 1h; Inert atmosphere; | 97% |
potassium cyanate
N-methylcyclohexylamine
para-nitrophenyl bromide
1-cyclohexyl-3-(4-nitrophenyl)-1-methyl-urea
Conditions | Yield |
---|---|
With copper(I) oxide; 2-(2,6-dimethylphenyl-amino)-2-oxoacetic acid potassium salt In acetonitrile at 110℃; Schlenk technique; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; potassium hydroxide In dimethyl sulfoxide at 120℃; for 0.5h; | 97% |
With sodium t-butanolate In dimethyl sulfoxide at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry; | 95% |
With sodium t-butanolate In dimethyl sulfoxide at 110℃; for 12h; Buchwald-Hartwig Coupling; | 87% |
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 0.666667h; | 75% |
With copper(l) iodide; cesium fluoride In dimethyl sulfoxide at 130℃; for 24h; Ullmann Condensation; Inert atmosphere; Glovebox; |
Conditions | Yield |
---|---|
In methanol; water for 0.25h; Inert atmosphere; | 97% |
N-methylcyclohexylamine
ethyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
2-(3-Cyclohexyl-3-methyl-thioureido)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
In dichloromethane for 5h; Ambient temperature; | 96% |
In dichloromethane at 20℃; for 3h; |
N-methylcyclohexylamine
cyclohexanone
N-cyclohexyl-N-methylcyclohex-1-enamine
Conditions | Yield |
---|---|
With titanium tetrachloride In cyclohexane at 0 - 20℃; Inert atmosphere; | 96% |
N-methylcyclohexylamine
o-bromobenzenesulfonyl chloride
2-bromo-N-cyclohexyl-N-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: N-methylcyclohexylamine; 4-tert-butylphenyl triflate With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 80℃; for 16h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere; | 96% |
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