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Synthetic route

sarcosine
107-97-1

sarcosine

A

formaldehyd
50-00-0

formaldehyd

B

carbon dioxide
124-38-9

carbon dioxide

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium perchlorate; chlorine at 24.9℃; Mechanism; Rate constant; Equilibrium constant; multistep reaction: 1.) water, 298 deg K, 2.) water, 298 deg K; reactions under var. conditions;A 100%
B n/a
C n/a
N-chloro-sarcosine
52316-59-3

N-chloro-sarcosine

A

formaldehyd
50-00-0

formaldehyd

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In water at 24.9℃; Rate constant; Mechanism; Thermodynamic data; Irradiation; I=0.5 mol-1 L-1; various pH; ΔH(excit.), ΔS(excit.);A 100%
B n/a
With water In 1,4-dioxane at 25℃;
With water In 1,4-dioxane at 25℃; Kinetics; Mechanism;
acetamide
60-35-5

acetamide

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

ethylbis(dimethyl(2-penten-2-yl)silyloxy)borane
111869-87-5

ethylbis(dimethyl(2-penten-2-yl)silyloxy)borane

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene dropwise addn. of acetamide to boron compd. soln., 160°C, 3.5h; heating (reflux), 10h; evapn.; all under Ar; distn.; elem. anal.;A 100%
B 98%
nitromethane
75-52-5

nitromethane

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With borane-ammonia complex In methanol; water at 20℃; for 0.0833333h;99%
With ammonia borane; Pd/MIL-101 In methanol; water at 20℃; for 0.025h;99%
With sodium tetrahydroborate In methanol; water at 20℃; for 0.0666667h; Sealed tube; Green chemistry;99%
piperidine
110-89-4

piperidine

N-n-butyl-N-methylamine
110-68-9

N-n-butyl-N-methylamine

A

1-butyl-piperidine
4945-48-6

1-butyl-piperidine

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
palladium at 160℃; for 5h;A 98%
B n/a
piperidine
110-89-4

piperidine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-Benzylpiperidine
2905-56-8

N-Benzylpiperidine

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
palladium at 130℃; for 10h;A 97%
B n/a
1-methyl-2-methylamino-4-imino-6-(2,3-dimethylguanidino)-1,4-dihydro-1,3,5-triazine

1-methyl-2-methylamino-4-imino-6-(2,3-dimethylguanidino)-1,4-dihydro-1,3,5-triazine

A

1-methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
6726-47-2

1-methyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione

B

N,N'-dimethyl-guanidine
3324-71-8

N,N'-dimethyl-guanidine

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With hydrogenchloride for 10h; Heating;A 15%
B 96%
C 4%
N,N'-Dimethylurea
96-31-1

N,N'-Dimethylurea

sodium p-toluenesulfonamide
18522-92-4

sodium p-toluenesulfonamide

A

N-Methyl-N'-toluene-p-sulfonylurea
13909-69-8

N-Methyl-N'-toluene-p-sulfonylurea

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
at 160℃; for 3h; Product distribution; Rate constant; Equilibrium constant; Other temperature, other time, other ratio of reactants, activation energy, ΔH, ΔS;;A 95.5%
B n/a
at 160℃; for 3h;A 95.5%
B n/a
ethylenediamine
107-15-3

ethylenediamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

methylamine
74-89-5

methylamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

Conditions
ConditionsYield
palladium at 120℃; for 10h;A n/a
B 95%
4-Aminobutanol
13325-10-5

4-Aminobutanol

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{5.3.0}dec-3-ene
129363-73-1

4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{5.3.0}dec-3-ene

B

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclodecene
129363-50-4

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclodecene

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-80°C, 4h;; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5;A n/a
B n/a
C 95%
6-methyl-8-nitro-1,6-naphthyridin-5(6H)-one
79878-19-6

6-methyl-8-nitro-1,6-naphthyridin-5(6H)-one

A

8-methylpyrido<2,3-d>pyridazin-5-one
90004-07-2

8-methylpyrido<2,3-d>pyridazin-5-one

B

methylamine
74-89-5

methylamine

C

NH3

NH3

Conditions
ConditionsYield
With hydrazine hydrate at 130 - 140℃; for 5h;A 94%
B n/a
C n/a
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

ethanolamine
141-43-5

ethanolamine

A

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-47-9

4,5-diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene heating under Ar, 40-70°C, 4h;A 93%
B 93%
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20°C, 24h;; distn. (vac.); elem. anal.;A 82%
B 87%
(2R)-2-aminobutan-1-ol
5856-63-3

(2R)-2-aminobutan-1-ol

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

(R)-4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene
129444-01-5

(R)-4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene

B

(R)-4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129444-00-4

(R)-4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 18h; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5;A n/a
B n/a
C 91%
pyrrolidine
123-75-1

pyrrolidine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-benzylcyclohexylamine
4383-25-9

N-benzylcyclohexylamine

B

N-phenyl(methylidene)cyclohexanamine
2211-66-7

N-phenyl(methylidene)cyclohexanamine

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
palladium at 120℃; for 10h;A 10%
B 90%
C n/a
2-aminobutanol
96-20-8, 13054-87-0

2-aminobutanol

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene
129363-71-9

4,5,7-triethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene

B

4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-48-0

4,5,7-triethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 22h; distn. (vac.); elem. anal.; monocyclic: bicyclic isomer = 95:5;A n/a
B n/a
C 89%
N-methylisoephedrine
160745-23-3

N-methylisoephedrine

A

2-hydroxy-1-phenylpropylamine
52500-61-5

2-hydroxy-1-phenylpropylamine

B

formaldehyd
50-00-0

formaldehyd

C

benzaldehyde
100-52-7

benzaldehyde

D

acetaldehyde
75-07-0

acetaldehyde

E

dimethyl amine
124-40-3

dimethyl amine

F

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With water at 25℃; Product distribution; Mechanism; anodic oxidation, carbonate buffer, pH 10; effect of substituents investigated with different types of β-alkanolamines;A 1.3%
B 28%
C 82%
D 88%
E 38%
F 33%
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

m-Hydroxyaniline
591-27-5

m-Hydroxyaniline

A

C30H48B2N2O2Si2
129390-09-6

C30H48B2N2O2Si2

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene at 125-150°C, 26h under Ar; evapn.; elem. anal.;A n/a
B 88%
N-methylalanine
3913-67-5

N-methylalanine

A

carbon dioxide
124-38-9

carbon dioxide

B

acetaldehyde
75-07-0

acetaldehyde

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium perchlorate; chlorine at 24.9℃; Mechanism; Rate constant; Equilibrium constant; multistep reaction: 1.) water, 298 deg K, 2.) water, 298 deg K; reactions under var. conditions;A n/a
B 87%
C n/a
2-methylamino-1-phenylpropanol
299-42-3

2-methylamino-1-phenylpropanol

A

formaldehyd
50-00-0

formaldehyd

B

benzaldehyde
100-52-7

benzaldehyde

C

acetaldehyde
75-07-0

acetaldehyde

D

benzoic acid
65-85-0

benzoic acid

E

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
Mechanism; Product distribution; anodic oxidation;A 12%
B 65%
C 68%
D 12%
E 87%
4,5-diethyl-2,5-dihydro-3-isopropenyl-1,2,2-trimethyl-1,2,5-azasilaborole
81620-70-4

4,5-diethyl-2,5-dihydro-3-isopropenyl-1,2,2-trimethyl-1,2,5-azasilaborole

ethanolamine
141-43-5

ethanolamine

A

4,5-diethyl-3-isopropenyl-2,2-dimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-59-3

4,5-diethyl-3-isopropenyl-2,2-dimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

4,5-diethyl-3-isopropenyl-2,2-dimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene
129363-70-8

4,5-diethyl-3-isopropenyl-2,2-dimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{3.3.0}oct-3-ene

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-25°C, 22h;; distn. (vac.); standing at room temp.; crystn. of bicyclic isomer; elem. anal.;A 57%
B n/a
C 87%
4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

A

4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{4.3.0}non-3-ene
129363-72-0

4,5-diethyl-2,2,3-trimethyl-6-oxa-1-azonia-2-sila-5-boratabicyclo{4.3.0}non-3-ene

B

4,5-Diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclononene
129363-49-1

4,5-Diethyl-2,2,3-trimethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclononene

C

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) addn. of boron compd. to equimolar amt. of aminoalkanol, room temp.; driving out CH3NH2 in a stream of Ar, 20-80°C, 24h;; distn. (vac.); elem. anal.; monocyclic : bicyclic isomer = 95:5;A n/a
B n/a
C 87%
pseudoephedrine
90-82-4

pseudoephedrine

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

(4S,5S)-2-Ethyl-4-methyl-5-phenyl-1,3,2-oxazaborolan
129363-65-1

(4S,5S)-2-Ethyl-4-methyl-5-phenyl-1,3,2-oxazaborolan

B

{(1S,2S)-2-[Dimethyl-((E)-1-methyl-but-1-enyl)-silanyloxy]-1-methyl-2-phenyl-ethyl}-methyl-amine
129363-66-2

{(1S,2S)-2-[Dimethyl-((E)-1-methyl-but-1-enyl)-silanyloxy]-1-methyl-2-phenyl-ethyl}-methyl-amine

C

(7S,8S)-4,5-Diethyl-2,2,3,6,7-pentamethyl-8-phenyl-1-oxa-6-aza-2-sila-5-bora-3-cycloocten
129443-99-8

(7S,8S)-4,5-Diethyl-2,2,3,6,7-pentamethyl-8-phenyl-1-oxa-6-aza-2-sila-5-bora-3-cycloocten

D

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In 1,2,5-trimethyl-benzene dropwise addn. of boron compd. to aminoalkanol soln. under Ar, 0.5h; heating to 140-150°C, 12h; evapn.; distn. (vac.); elem. anal.;A n/a
B n/a
C 75%
D 86%
acetamide
60-35-5

acetamide

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
With sodium hydroxide; benzyltrimethylazanium tribroman-2-uide In water at 70℃; for 2h;85%
With potassium hydroxide; bromine ueber mehrere Stufen;
With potassium hydroxide; bromine
With water; bromine; calcium carbonate ueber mehrere Stufen;
With sodium hydroxide; sodium bromite In water at 70℃; for 0.5h; Yield given;
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-methyldibenzylamine
102-05-6

N-methyldibenzylamine

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
palladium at 120℃; for 20h;A 85%
B n/a
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

(E)-3-<<2-(Dimethylamino)ethoxy>ethylboryl>-2-<<2-(dimethylamino)ethoxy>dimethylsilyl>-2-penten
129363-54-8

(E)-3-<<2-(Dimethylamino)ethoxy>ethylboryl>-2-<<2-(dimethylamino)ethoxy>dimethylsilyl>-2-penten

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) stirring under Ar, 0-20°C, 1-2h; heating to a maximum of 140°C, 10h; distn. (vac.); elem. anal.;A 82%
B 76%
(2-hydroxyethyl)(methyl)amine
109-83-1

(2-hydroxyethyl)(methyl)amine

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

4,5-diethyl-2,2,3,6-tetramethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-52-6

4,5-diethyl-2,2,3,6-tetramethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) dropwise addn. of boron compd. to aminoalkanol, 10 min; stirring in a stream of Ar, 20°C, 24h;; distn. (vac.); elem. anal.;A 81%
B 82%
trimethyl-borane; compound with methylamine
854457-30-0

trimethyl-borane; compound with methylamine

A

trimethylborane
593-90-8

trimethylborane

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
at 130.0°C, 77.4 Torr equilibrium;A 81.95%
B 81.95%
at 130.0°C, 77.4 Torr equilibrium;A 81.95%
B 81.95%
at 85.4°C, 52.5 Torr equilibrium;A 38.86%
B 38.86%
at 85.4°C, 52.5 Torr equilibrium;A 38.86%
B 38.86%
L(-)-ephedrine hemihydrate
299-42-3

L(-)-ephedrine hemihydrate

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole
79483-05-9

4,5-diethyl-2,5-dihydro-1,2,2,3-tetramethyl-1H-1,2,5-azasilaborole

A

(7S,8R)-4,5-diethyl-2,2,3,6,7-pentamethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene
129363-53-7

(7S,8R)-4,5-diethyl-2,2,3,6,7-pentamethyl-1-oxa-6-aza-2-sila-5-bora-3-cyclooctene

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
In neat (no solvent) dropwise addn. of boron compd. to aminoalkanol under Ar, 5 min; heating to 110-150°C, 8.5h;; distn. (vac.); elem. anal.;A 73%
B 80.5%
N-n-butyl-N-methylamine
110-68-9

N-n-butyl-N-methylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

A

N-Butyl-N-methylbenzenemethanamine
31844-65-2

N-Butyl-N-methylbenzenemethanamine

B

methylamine
74-89-5

methylamine

Conditions
ConditionsYield
palladium at 120℃; for 10h;A 80%
B n/a
Succinimide
123-56-8

Succinimide

methylamine
74-89-5

methylamine

N-methyl-succinic diamide
3025-97-6

N-methyl-succinic diamide

Conditions
ConditionsYield
at 20℃; under 600.048 - 750.06 Torr; Addition; soid-gas reaction; ring cleavage;100%
With water
In water for 1h; Ambient temperature;
Indole-3-carboxaldehyde
487-89-8

Indole-3-carboxaldehyde

methylamine
74-89-5

methylamine

3-(N-methylformimidoyl)-1H-indole
22980-06-9

3-(N-methylformimidoyl)-1H-indole

Conditions
ConditionsYield
With magnesium sulfate In methanol; dichloromethane for 7h; Heating;100%
With water
In water 1.) 40 - 45 deg C, 15 min, 2.) room temp., 4 h; Yield given;
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methylamine
74-89-5

methylamine

2-methylisoindolin-1-one
5342-91-6

2-methylisoindolin-1-one

Conditions
ConditionsYield
In water at 220℃; under 114000 Torr; for 4h;100%
With ethanol at 220℃;
In 5,5-dimethyl-1,3-cyclohexadiene
phthalimide
136918-14-4

phthalimide

methylamine
74-89-5

methylamine

N1,N2-dimethylphthalamide
19532-98-0

N1,N2-dimethylphthalamide

Conditions
ConditionsYield
at -20℃; under 75.006 Torr; Addition; solid-gas reaction; ring cleavage;100%
In ethanol55%
1,8-Naphthalic anhydride
81-84-5

1,8-Naphthalic anhydride

methylamine
74-89-5

methylamine

N-methylnaphthalimide
2382-08-3

N-methylnaphthalimide

Conditions
ConditionsYield
In ethanol; water at 20℃; for 72h; Inert atmosphere;100%
In water for 72h; Reflux;100%
In water100%
4-chloro-2-methylquinoline
4295-06-1

4-chloro-2-methylquinoline

methylamine
74-89-5

methylamine

N,2-dimethylquinolin-4-amine
21875-68-3

N,2-dimethylquinolin-4-amine

Conditions
ConditionsYield
In ethanol at 120℃; for 7h; Sealed tube; Microwave irradiation;100%
With ethanol at 120℃;
With phenol at 190℃;
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

methylamine
74-89-5

methylamine

p-methylbenzylidene-methylamine
17972-13-3, 29086-13-3, 53699-34-6

p-methylbenzylidene-methylamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In methanol; dichloromethane for 18h; Molecular sieve;86%
6-Chloropurine riboside
2004-06-0

6-Chloropurine riboside

methylamine
74-89-5

methylamine

N6-methyladenosine
1867-73-8

N6-methyladenosine

Conditions
ConditionsYield
With triethylamine In ethanol for 4h; Reflux;100%
In ethanol; water Sealed tube; Reflux;94%
In ethanol; water at 100℃; for 72h; Sealed tube;54%
benzaldehyde
100-52-7

benzaldehyde

methylamine
74-89-5

methylamine

N-Benzylidenemethylamine
622-29-7

N-Benzylidenemethylamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In water for 1h; Ambient temperature;95%
at 20℃; for 15h;95%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

methylamine
74-89-5

methylamine

4-(Methylimino-methyl)-phenol
5766-74-5

4-(Methylimino-methyl)-phenol

Conditions
ConditionsYield
at 0℃; under 187.515 Torr; Solid phase reaction; gas-solid reaction;100%
at 20℃; for 12h;100%
With ethanol; water at 40℃;
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

methylamine
74-89-5

methylamine

4-methoxybenzyl-N-methylimine
13114-23-3

4-methoxybenzyl-N-methylimine

Conditions
ConditionsYield
In ethanol; water at 40℃; for 2h;100%
In ethanol at 0 - 40℃;90%
In water for 10h; Ambient temperature;80%
salicylaldehyde
90-02-8

salicylaldehyde

methylamine
74-89-5

methylamine

2-(methyliminomethyl)phenol
3117-65-5

2-(methyliminomethyl)phenol

Conditions
ConditionsYield
In ethanol at 20℃; for 8h;100%
In ethanol at 20℃; for 8h;100%
With molecular sieve In ethanol; water for 0.5h;96%
N,N,N',N'-Tetramethylphosphorodiamidic chloride
1605-65-8

N,N,N',N'-Tetramethylphosphorodiamidic chloride

methylamine
74-89-5

methylamine

Pentamethylphosphoramide
10159-46-3

Pentamethylphosphoramide

Conditions
ConditionsYield
at 20℃; for 48h;100%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane at 0℃; for 1h;83%
64%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

methylamine
74-89-5

methylamine

N-(3,4-dimethoxybenzylidene)methanamine
17972-14-4

N-(3,4-dimethoxybenzylidene)methanamine

Conditions
ConditionsYield
With 4 A molecular sieve In toluene at 0℃;100%
With benzene
In methanol at 40℃; for 5h;
In ethanol at 50℃;
In benzene for 2h; Reflux;
meta-hydroxybenzaldehyde
100-83-4

meta-hydroxybenzaldehyde

methylamine
74-89-5

methylamine

3-(Methylimino-methyl)-phenol
7221-33-2

3-(Methylimino-methyl)-phenol

Conditions
ConditionsYield
In ethanol at 0 - 5℃; for 2h;100%
at 20℃; for 12h;100%
With benzene zuletzt unter Abdestillieren des gebildeten Wassers;
methyl thioisocyanate
556-61-6

methyl thioisocyanate

methylamine
74-89-5

methylamine

N,N-dimethylthiourea
534-13-4

N,N-dimethylthiourea

Conditions
ConditionsYield
at 0℃; under 375.03 Torr; Addition; solid-gas reaction;100%
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methylamine
74-89-5

methylamine

methyl 3-(methylamino)propanoate
24549-12-0

methyl 3-(methylamino)propanoate

Conditions
ConditionsYield
In diethyl ether at 4℃; Addition;100%
With C12H18NO3S(1+)*HO4S(1-) at 25℃; for 0.0833333h; Ionic liquid; Neat (no solvent); chemoselective reaction;99%
In ethanol at -10℃;86%
acetophenone
98-86-2

acetophenone

methylamine
74-89-5

methylamine

N-(1-phenylethylidene)methanamine
6907-71-7

N-(1-phenylethylidene)methanamine

Conditions
ConditionsYield
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere;100%
In ethanol at 20℃; for 48h; Molecular sieve; Inert atmosphere;100%
With triethylamine In ethanol for 1h; Molecular sieve;97%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

methylamine
74-89-5

methylamine

N-(3-methoxybenzylidene)methanamine
16928-30-6

N-(3-methoxybenzylidene)methanamine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In ethanol at 0 - 40℃;90%
In water for 10h; Ambient temperature;86%
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

methylamine
74-89-5

methylamine

1-(2-methoxyphenyl)-N-methylmethanimine
1125-90-2

1-(2-methoxyphenyl)-N-methylmethanimine

Conditions
ConditionsYield
In ethanol at 0 - 40℃;100%
In water for 10h; Ambient temperature;80%
With water
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

methylamine
74-89-5

methylamine

4-(dimethylamino)-N-methylbenzylimine
877-79-2

4-(dimethylamino)-N-methylbenzylimine

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Solid phase reaction; gas-solid reaction;100%
at 20℃; for 12h;100%
With benzene
ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

methylamine
74-89-5

methylamine

2-nitro-N-methylaniline
612-28-2

2-nitro-N-methylaniline

Conditions
ConditionsYield
In ethanol; water Reflux;100%
In methanol; water Heating;98%
In water at 20℃; for 2h; Inert atmosphere;93%
1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

methylamine
74-89-5

methylamine

N-methyl-2,4-dinitroaniline
2044-88-4

N-methyl-2,4-dinitroaniline

Conditions
ConditionsYield
In ethanol at 20℃; for 15h;100%
In ethanol; water at 20℃; for 1h;100%
In ethanol at 0 - 20℃; for 15h;95%
1-isothiocyanatonaphthalene
551-06-4

1-isothiocyanatonaphthalene

methylamine
74-89-5

methylamine

1-methyl-3-naphthalene-1-yl-thiourea
2740-98-9

1-methyl-3-naphthalene-1-yl-thiourea

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;100%
With ethanol
p-nitrophenyl isothiocyanate
2131-61-5

p-nitrophenyl isothiocyanate

methylamine
74-89-5

methylamine

1-(4-nitrophenyl)-3-methyl-thiourea
16361-69-6

1-(4-nitrophenyl)-3-methyl-thiourea

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;100%
methylamine
74-89-5

methylamine

β-naphthol
135-19-3

β-naphthol

2-N-methylaminonaphthalene
2216-67-3

2-N-methylaminonaphthalene

Conditions
ConditionsYield
With ammonium chloride In ethanol at 200℃; for 20h;100%
With water at 200 - 220℃; unter Druck;
With sodium hydrogensulfite In water Bucherer reaction; Autoclave;
methylamine
74-89-5

methylamine

3-(bromomethyl)benzonitrile
28188-41-2

3-(bromomethyl)benzonitrile

3-((methylamino)methyl)benzonitrile
90389-96-1

3-((methylamino)methyl)benzonitrile

Conditions
ConditionsYield
In THjfF (tetrahydrofuran) at 20℃; for 3h; Inert atmosphere;100%
In tetrahydrofuran at 20℃; for 24h;96%
In water at 0 - 20℃; for 3.16h;82%
methylamine
74-89-5

methylamine

4-Bromophenyl isothiocyanate
1985-12-2

4-Bromophenyl isothiocyanate

1-(4-bromophenyl)-3-methyl-thiourea
61449-55-6

1-(4-bromophenyl)-3-methyl-thiourea

Conditions
ConditionsYield
at 20℃; under 750.06 Torr; Addition; solid-gas reaction;100%
With ethanol
methylamine
74-89-5

methylamine

2,3-dimethyoxybenzaldehyde
86-51-1

2,3-dimethyoxybenzaldehyde

(2,3-dimethoxy-benzylidene)-methyl-amine
722495-95-6

(2,3-dimethoxy-benzylidene)-methyl-amine

Conditions
ConditionsYield
at 20℃; for 12h;100%
In ethanol at 0 - 40℃;90%
With benzene zuletzt unter Erwaermen und Entfernen des gebildeten Wassers;
In benzene for 2h; Reflux;
In ethanol; water
methylamine
74-89-5

methylamine

2,4-Dichloro-5-nitropyrimidine
49845-33-2

2,4-Dichloro-5-nitropyrimidine

2-chloro-4-(methylamino)-5-nitropyrimidine
89283-49-8

2-chloro-4-(methylamino)-5-nitropyrimidine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at -78 - 20℃; for 3h;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -60℃; for 1h;85%
With N-ethyl-N,N-diisopropylamine In ethanol; dichloromethane at 0℃; for 0.5h;85.4%

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