• Name

  6-Aminomethyl-6,11-dihydro-5H-dibenz[b,e]azepine (E)-2-butenedioate

• EINECS 685-627-3
• CAS No. 127785-96-0
• Article Data3
• CAS DataBase
• Density
• Solubility
• Melting Point 194-195 °C (decomp)
• Formula C₁₅H₁₆N₂^.C₄H₄O₄
• Boiling Point 616.9 °C at 760 mmHg
• Molecular Weight 340.379
• Flash Point Flash Point: 326.9 °C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 5H-dibenz[b,e]azepine-6-methanamine, 6,11-dihydro-, (2E)-2-butenedioate (1:1);Epinastine Intermediate;1-(6,11-Dihydro-5H-dibenzo[b,e]azepin-6-yl)methanamine (2E)-but-2-enedioate (1:1);6-Amiomethyl-6,11-dihydro-5H-dibenz[b,e]azepin(E)-2-butanedioate(1:1);
• PSA 112.65000
• LogP 3.25280

Synthetic route

74860-00-7

N-<(11H-dibenzazepin-6-yl)methyl>phthalimide

110-17-8

(2E)-but-2-enedioic acid

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

Conditions

Conditions	Yield
Stage #1: N-<(11H-dibenzazepin-6-yl)methyl>phthalimide With sodium tetrahydroborate In methanol; water; isopropyl alcohol; toluene at 20 - 30℃; for 24.5h; Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20 - 80℃; for 1.5h; Stage #3: (2E)-but-2-enedioic acid With sodium hydroxide Product distribution / selectivity; more than 3 stages;	76.1%
Stage #1: N-<(11H-dibenzazepin-6-yl)methyl>phthalimide With sodium tetrahydroborate In methanol; water; isopropyl alcohol; toluene at 20 - 30℃; for 24.5h; Stage #2: With methanol; sodium hydroxide In water; isopropyl alcohol at 20 - 80℃; for 1.5h; Stage #3: (2E)-but-2-enedioic acid In methanol at 0 - 20℃; for 3h; Product distribution / selectivity;	72.4%
Stage #1: N-<(11H-dibenzazepin-6-yl)methyl>phthalimide With sodium tetrahydroborate In water; isopropyl alcohol at 20 - 30℃; for 24.5h; Stage #2: With acetic acid In water; isopropyl alcohol at 20 - 80℃; for 1.5h; Stage #3: (2E)-but-2-enedioic acid With sodium hydroxide Product distribution / selectivity; more than 3 stages;	69%

41218-84-2

6-aminomethyl-6,11-dihydro-5H-dibenzo[b,e]azepine

110-17-8

(2E)-but-2-enedioic acid

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

Conditions

Conditions	Yield
In methanol at 20℃; for 1h;	76%
In methanol at 35 - 40℃; for 1.5 - 1.66667h;

21535-43-3

N-[2-(phenylmethyl)phenyl]-2-chloroacetamide

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate / toluene / 6 h / 65 - 90 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 55 °C 2.2: 15 h / 45 °C 3.1: formic acid; hydrogen; 5%-palladium/activated carbon / N,N-dimethyl-formamide / 24 h / 70 °C / 7500.75 Torr 4.1: hydrogenchloride / glycerol; water / 2.5 h / 20 - 110 °C 5.1: methanol / 1 h / 20 °C View Scheme

21535-44-4

6-(chloromethyl)-11H-dibenzazepine

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium hydroxide / N,N-dimethyl-formamide / 55 °C 1.2: 15 h / 45 °C 2.1: formic acid; hydrogen; 5%-palladium/activated carbon / N,N-dimethyl-formamide / 24 h / 70 °C / 7500.75 Torr 3.1: hydrogenchloride / glycerol; water / 2.5 h / 20 - 110 °C 4.1: methanol / 1 h / 20 °C View Scheme

6-cyclopropylaminomethyl-5H-dibenz(b,e)azepine

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: formic acid; hydrogen; 5%-palladium/activated carbon / N,N-dimethyl-formamide / 24 h / 70 °C / 7500.75 Torr 2: hydrogenchloride / glycerol; water / 2.5 h / 20 - 110 °C 3: methanol / 1 h / 20 °C View Scheme

6-cyclopropylaminomethyl-6,11-dihydro-5H-dibenz(b,e)azepine

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / glycerol; water / 2.5 h / 20 - 110 °C 2: methanol / 1 h / 20 °C View Scheme

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

40943-37-1

O-methyl-N-(methoxycarbonyl)-isourea

{imino[N-(5H-dibenz[b,e]azepin-6-yl)methylamino]methyl}carbamate

Conditions

Conditions	Yield
In dimethyl sulfoxide at 40℃; for 22h; Solvent;	94%

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

80012-43-7

epinastine

Conditions

Conditions	Yield
With sodium hydroxide In water at 25 - 30℃; for 0.5h;

N-(iminomethoxymethyl)allylcarbamate

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

{imino[N-(5H-dibenz[b,e]azepin-6-yl)methylamino]allyl}carbamate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 21h;

127785-96-0

6,11-dihydro-5H-dibenzazepine-6-methanamine fumarate

3-amino-9,13b-dihydro-1H-dibenzo[c,f]imidazo[1,5-a]azepine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethyl sulfoxide / 22 h / 40 °C 2: acetic acid / toluene / 23 h / 90 °C View Scheme

6-Aminomethyl-6,11-dihydro-5H-dibenz[b,e]azepine (E)-2-butenedioate Specification