494-19-9

Basic information

• Product Name: Iminodibenzyl
• Synonyms: TIMTEC-BB SBB003595;10,11-Dihydro-5-dibenz(b,f)azepine;10,11-Dihydrodibenz[b,f]azepine;2,2’-iminobibenzyl;2,2'-Iminobibenzyl;3,4-Dihydro-2.36.7-dibenzazepine;5H-Dibenzo[b,f]azepine, 10,11-dihydro-;f)azepine,10,11-dihydro-5h-dibenz(
• CAS NO: 494-19-9
• Molecular Formula: C₁₄H₁₃N
• Molecular Weight: 195.26
• EINECS: 207-787-1
• Product Categories: Miscellaneous;Aromatics, Enzyme substrates, Heterocycles, Metabolites & Impurities
• Mol File: 494-19-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: 105-108 °C(lit.)
• Boiling Point: 321.94°C (rough estimate)
• Flash Point: 161.3 °C
• Appearance: Yellow to beige/Crystalline Powder
• Density: 1.0778 (rough estimate)
• Vapor Pressure: 0.000199mmHg at 25°C
• Refractive Index: 1.6353 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)
• PKA: 0.83±0.20(Predicted)
• BRN: 152732
• CAS DataBase Reference: Iminodibenzyl(CAS DataBase Reference)
• NIST Chemistry Reference: Iminodibenzyl(494-19-9)
• EPA Substance Registry System: Iminodibenzyl(494-19-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 22-24/25-39-26-36/37/39-27
• WGK Germany: 3
• RTECS: HN8950000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 494-19-9(Hazardous Substances Data)

Usage

Description

Iminodibenzyl was not a new drug. It had been discovered in 1898 and used briefly as an intermediate, in the preparation of Sky Blue, a dye stuff. Iminodibenzyl, however, had a tricyclic ring structure, similar in appearance to the phenothiazines. Iminodibenzyl is an important drug intermediate, which can be used for the medicine synthesis as a tristimania and epilepsia.

Uses

Different sources of media describe the Uses of 494-19-9 differently. You can refer to the following data:
1. 10,11-Dihydro-5H-dibenzo[b,f]azepine is a metabolite of the tricyclic antidepressant, Imipramine (I465980). 10,11-Dihydro-5H-dibenzo[b,f]azepine can be used as a chromogenic probe for the quantification of hydrogen peroxide and glucose.
2. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Preparation

Iminodibenzyl is obtained from o-nitrotoluene by condensation, reduction and cyclization.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

InChI:InChI=1/C14H13N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-8,15H,9-10H2

Synthetic route

5-acetyliminodibenzyl (13080-75-6) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	99%
Stage #1: 5-acetyliminodibenzyl With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	99%
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

5-propionyl-10,11-dihydro-5H-dibenzo[b,f]azepine (40583-89-9) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	99%
Stage #1: 5-propionyl-10,11-dihydro-5H-dibenzo[b,f]azepine With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	81%
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

dibenzoazepine (256-96-2) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With [Fe3(1,1,1,3,3,3-hexamethyldisilazan-2-ide)4]Fe(η6-toluene); hydrogen at 20℃; under 1425.14 Torr; for 3h; Inert atmosphere; Glovebox; chemoselective reaction;	92%
With tetraethylammonium perchlorate; ammonium chloride In water; N,N-dimethyl-formamide cathodic (Hg, -2.0 V vs. SCE) reduction;	82%

dibenzoazepine (256-96-2) → 9-methyl-acridine (611-64-3) + 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With iodine; hypophosphorous acid In acetic acid for 24h; Heating;	A 92% B 8%

10,11-dihydro-dibenzo[b,f]azepine-5-carbonyl chloride (33948-19-5) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
In acetonitrile electrolysis (Et4NClO4, Hg-dropelectrode);	90%

10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid prop-2-ynyl ester → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 25℃; for 0.75h; sonicated;	88%

C18H19NO → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
Stage #1: C18H19NO With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	87%
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	86%
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

C14H13Br2N → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With C55H46N4O4W; potassium carbonate; N-ethyl-N,N-diisopropylamine In acetonitrile for 12h; Inert atmosphere; Irradiation;	68%

C21H25NO → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	67%
Stage #1: C21H25NO With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	62%
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

5-acetyliminodibenzyl (13080-75-6) → 9,10-dihydrodibenzazepine (494-19-9) + 11-ethyliminodibenzyl (40583-88-8) + ethanol (64-17-5)

Conditions	Yield
With Mo2((1)-H)2(OtBu)6; diphenylsilane In toluene for 25h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Reflux;	A 62% B 36% C n/a

sodium cyanide (773837-37-9) + impramine (50-49-7) → 9,10-dihydrodibenzazepine (494-19-9) + 2-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-(methyl)amino)acetonitrile + 2-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-4-(dimethylamino)butanenitrile

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; acetic acid In acetonitrile at 20℃; for 24h; Irradiation; Sealed tube;	A 50% B 22% C 23%

dibenzoazepine (256-96-2) + acetic acid (64-19-7) → 9-methyl-acridine (611-64-3) + 5-acetyliminodibenzyl (13080-75-6) + 9-methyl-9,10-dihydroacridine (4217-52-1) + 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With iodine; hypophosphorous acid for 96h; Heating;	A 18% B 9% C 20% D 47%

2-bromophenylacetyl chloride (55116-09-1) + aniline (62-53-3) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
Stage #1: aniline With copper(l) iodide; n-butyllithium; tetraethylammonium bromide; triethylamine In tetrahydrofuran at -50℃; for 4h; Inert atmosphere; Stage #2: 2-bromophenylacetyl chloride In tetrahydrofuran at 70℃; for 5h; Inert atmosphere;	45.7%

1-nitro-2-phenethylbenzene (6796-01-6) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With trifluoroacetic acid; zinc	45%

potassium cyanide + impramine (50-49-7) → 9,10-dihydrodibenzazepine (494-19-9) + 2-((3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propyl)-(methyl)amino)acetonitrile + 2-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-4-(dimethylamino)butanenitrile

Conditions	Yield
With 2-Picolinic acid; iron(III) chloride; tert-Butyl peroxybenzoate; 18-crown-6 ether In acetonitrile at 50℃; for 48h;	A 6% B 35% C 15%

5-[3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-4-methylene-4,5-dihydro-isoxazol-5-yl]-10,11-dihydro-5H-dibenzo[b,f]azepine (152700-41-9) → 9,10-dihydrodibenzazepine (494-19-9) + 4-Chloromethyl-3-(3,5-dichloro-2,4,6-trimethyl-phenyl)-isoxazole + 5-[3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-isoxazol-(4Z)-ylidenemethyl]-10,11-dihydro-5H-dibenzo[b,f]azepine + 4-[3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-isoxazol-4-ylmethyl]-10,11-dihydro-5H-dibenzo[b,f]azepine

Conditions	Yield
With zinc(II) chloride In toluene for 6h; Heating; Further byproducts given;	A 14% B 3% C 33% D 22%

Imipramine hydrochloride (113-52-0) → desipramine (50-47-5) + 9,10-dihydrodibenzazepine (494-19-9) + 10-Hydroxyimipramine (796-28-1)

Conditions	Yield
In water Ambient temperature; M. griseo-cyanus (ATCC 1207a); further microbial agents;	A 10 mg B n/a C n/a

Imipramine hydrochloride (113-52-0) → desipramine (50-47-5) + 9,10-dihydrodibenzazepine (494-19-9) + 10-Hydroxyimipramine (796-28-1) + 2-hydroxyimipramine (303-70-8)

Conditions	Yield
In water for 480h; Ambient temperature; C. blakesleeana (ATCC 8688a); further microbial agents; Further byproducts given;	A n/a B n/a C 30 mg D 88 mg

Imipramine hydrochloride (113-52-0) → 9,10-dihydrodibenzazepine (494-19-9) + 10-Hydroxyimipramine (796-28-1) + 2-hydroxyimipramine (303-70-8) + imipramine N-oxide (6829-98-7)

Conditions	Yield
In water; N,N-dimethyl-formamide for 480h; Ambient temperature; C. blakesleeana (ATCC 8688a); further microbial agents; Further byproducts given;	A n/a B 30 mg C 88 mg D n/a

Imipramine hydrochloride (113-52-0) → 9,10-dihydrodibenzazepine (494-19-9) + imipramine N-oxide (6829-98-7)

Conditions	Yield
In water; N,N-dimethyl-formamide for 360h; Ambient temperature; F. oxysporum f. sp. cepae (ATCC 11711); further microbial agents;	A 7 mg B n/a
In water for 312h; Ambient temperature; A. flavipes (ATCC 16795); further microbial agents;	A n/a B 112 mg

5-[3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-4-methylene-4,5-dihydro-isoxazol-5-yl]-10,11-dihydro-5H-dibenzo[b,f]azepine (152700-41-9) → 9,10-dihydrodibenzazepine (494-19-9) + 3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-isoxazole-4-carbaldehyde

Conditions	Yield
With zinc(II) iodide In toluene for 6h; Heating;

5-[3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-isoxazol-(4Z)-ylidenemethyl]-10,11-dihydro-5H-dibenzo[b,f]azepine → 9,10-dihydrodibenzazepine (494-19-9) + 3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-isoxazole-4-carbaldehyde

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 4h; Heating;

dibenzoazepine (256-96-2) + o-toluidine (95-53-4) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
palladium on activated charcoal at 230℃; Rate constant;

2,2'-ethylenedianiline (34124-14-6) + hydrochloride of salt of 2.2'-diamino-dibenzyl → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
at 265 - 275℃;

Imipramine hydrochloride (113-52-0) → 9,10-dihydrodibenzazepine (494-19-9) + Dimethyl-propylidene-ammonium

Conditions	Yield
at 280 - 326℃; Kinetics;

5-[3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-4-methylene-4,5-dihydro-isoxazol-5-yl]-10,11-dihydro-5H-dibenzo[b,f]azepine (152700-41-9) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 33 percent / ZnCl2 / toluene / 6 h / Heating 2: aq. HCl / dioxane / 4 h / Heating View Scheme

2,2'-diaminostilbene (617-20-9) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: isoamyl alcohol; sodium 2: 265 - 275 °C View Scheme

Imipramine hydrochloride (113-52-0) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
With peroxidase from horseradish type VI; dihydrogen peroxide at 37℃; for 1h; pH=7; aq. phosphate buffer; Enzymatic reaction;

2,2'-dinitrobibenzyl (16968-19-7) → 9,10-dihydrodibenzazepine (494-19-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen 2: hydrogenchloride / Heating View Scheme

9,10-dihydrodibenzazepine (494-19-9) → 2,4,6,8-tetrabromoiminodibenzyl (100527-68-2)

Conditions	Yield
With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 3h;	100%

9,10-dihydrodibenzazepine (494-19-9) + 9-bromophenanthrene (573-17-1) → N-(9-phenanthryl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	100%

1-bromo-4-methoxy-benzene (104-92-7) + 9,10-dihydrodibenzazepine (494-19-9) → 5-(4-methoxyphenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (91222-27-4)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	100%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Reagent/catalyst; Inert atmosphere;	91%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	91%

9,10-dihydrodibenzazepine (494-19-9) + allyl bromide (106-95-6) → 5-allyl-10,11-dihydro-5H-dibenzoazepine (74074-21-8)

Conditions	Yield
Stage #1: 9,10-dihydrodibenzazepine With sodium hydride In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide Inert atmosphere;	99%
Stage #1: 9,10-dihydrodibenzazepine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h; Inert atmosphere; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Inert atmosphere;	92%
	68%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 72h;	14%

9,10-dihydrodibenzazepine (494-19-9) + 4-chloromethoxybenzene (623-12-1) → 5-(4-methoxyphenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (91222-27-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; sodium t-butanolate In toluene at 20 - 135℃; for 20h; Buchwald-Hartwig reaction; Inert atmosphere;	99%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere;	87%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	87%

9,10-dihydrodibenzazepine (494-19-9) + chlorobenzene (108-90-7) → 10,11-dihydro-N-phenyldibenzazepine (78943-60-9)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	99%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere;	80%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	80%

9,10-dihydrodibenzazepine (494-19-9) → dibenzoazepine (256-96-2)

Conditions	Yield
With 1-methyl-2-nitrobenzene; palladium on activated charcoal at 230℃; for 1.5h; Rate constant; Kinetics; Thermodynamic data; var. hydrogen acceptors (also without acceptor); ΔH(excit.), ΔS(excit.); var. temp. and time;	98.2%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h;	24%
Stage #1: 9,10-dihydrodibenzazepine With N-Bromosuccinimide Stage #2: With pyridine

9,10-dihydrodibenzazepine (494-19-9) + (acetylamino)acetaldehyde dimethyl acetal (62005-48-5) → N-(2-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethyl)acetamide (1262142-12-0)

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction;	98%

9,10-dihydrodibenzazepine (494-19-9) + 2-methylphenyl bromide (95-46-5) → 5-(o-tolyl)-10,11-dihydro-5H-dibenzo[b,f]azepine

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;	81%

9,10-dihydrodibenzazepine (494-19-9) + 1-Bromonaphthalene (90-11-9) → N-(1-naphthyl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%

9,10-dihydrodibenzazepine (494-19-9) + 1-Bromo-4-fluorobenzene (460-00-4) → N-(4-fluorophenyl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Reagent/catalyst; Inert atmosphere;	82%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	82%
With nickel(II) oxide; potassium tert-butylate; triphenylphosphine In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;	73%

9,10-dihydrodibenzazepine (494-19-9) + 4-bromophenethanol (4654-39-1) → 2-(4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)phenyl)ethan-1-ol

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;	98%

2-bromo-1-benzothiophene (5394-13-8) + 9,10-dihydrodibenzazepine (494-19-9) → N-(2-benzothiophenyl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;	98%

9,10-dihydrodibenzazepine (494-19-9) + 2,6-dimethyl-1-chlorobenzene (6781-98-2) → N-(2,6-dimethylphenyl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	97%

2-bromo-pyridine (109-04-6) + 9,10-dihydrodibenzazepine (494-19-9) → 5-(pyridin-2-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	97%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In toluene at 120℃; for 48h; Inert atmosphere;	75%

9,10-dihydrodibenzazepine (494-19-9) + hexanoic acid (142-62-1) → 5-hexyl-10,11-dihydro-5H-dibenzo[b,f]azepine hydrochloride

Conditions	Yield
Stage #1: hexanoic acid With sodium tetrahydroborate In toluene at 0 - 5℃; Stage #2: 9,10-dihydrodibenzazepine With sodium tetrahydroborate In toluene at 25 - 80℃; for 5h; Stage #3: With hydrogenchloride In water; isopropyl alcohol	97%

9,10-dihydrodibenzazepine (494-19-9) → 2,8-dibromo-10,11-dihydro-5H-dibenzo[b,f]azepine (40583-96-8)

Conditions	Yield
With phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 4h; Inert atmosphere;	96%
With N-Bromosuccinimide In chloroform at 0 - 20℃; for 1h; Darkness;	78%
With N-Bromosuccinimide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 1h;	63%
With N-Bromosuccinimide In chloroform at 0 - 25℃; for 2h; Inert atmosphere;	41%
With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 0.2h; Yield given;

+ 9,10-dihydrodibenzazepine (494-19-9) → 10,11-dihydro-N-phenyldibenzazepine (78943-60-9)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	96%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	95%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	90%

9,10-dihydrodibenzazepine (494-19-9) → N-(2-biphenyl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	96%

9,10-dihydrodibenzazepine (494-19-9) + 9-Bromoanthracene (1564-64-3) → 5-(anthracen-9-yl)-10,11-dihydro-5H-dibenzo[b,f]azepine

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	96%
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; ruphos In 1,4-dioxane at 100℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;	75%

5-bromo-1H-indole (10075-50-0) + 9,10-dihydrodibenzazepine (494-19-9) → N-(5-indolyl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;	96%

9,10-dihydrodibenzazepine (494-19-9) + chloroacetyl chloride (79-04-9) → 2-chloro-1-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethan-1-one (3534-05-2)

Conditions	Yield
In toluene at 90℃; for 4h; Inert atmosphere;	95%
In toluene for 5h; Heating;	53%
In toluene Heating;
With benzene

9,10-dihydrodibenzazepine (494-19-9) + acetic anhydride (108-24-7) → 5-acetyliminodibenzyl (13080-75-6)

Conditions	Yield
for 3h; Reflux;	95%
With acetic acid at 110℃; for 2h;	84%

9,10-dihydrodibenzazepine (494-19-9) + para-chlorotoluene (106-43-4) → 5-(4-methylphenyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (155162-78-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; sodium t-butanolate In toluene at 20 - 135℃; for 20h; Buchwald-Hartwig reaction; Inert atmosphere;	94%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere;	81%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	81%

9,10-dihydrodibenzazepine (494-19-9) + 2-Bromo-m-xylene (576-22-7) → N-(2,6-dimethylphenyl)iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Reagent/catalyst; Inert atmosphere;	94%

9,10-dihydrodibenzazepine (494-19-9) + o-trifluoromethylphenyl bromide (392-83-6) → N-[2-(trifluoromethyl)phenyl]iminodibenzyl

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	94%

9,10-dihydrodibenzazepine (494-19-9) + 5-(cyano)dibenzothiophenium triflate → 10,11-dihydro-5H-dibenzo[b,f]azepine-5-carbonitrile

Conditions	Yield
With caesium carbonate In dichloromethane at 20℃; for 8h; Inert atmosphere;	94%

morpholine (110-91-8) + formaldehyd (50-00-0) + 9,10-dihydrodibenzazepine (494-19-9) → bis(morpholinomethyl)-2,8 dihydro-10,11 5H dibenzoazepine (64097-61-6)

Conditions	Yield
With acetic acid for 30h; Heating;	93%

Upstream product

• 256-96-2 dibenzoazepine 
• 33948-19-5 10,11-dihydro-dibenzo[b,f]azepine-5-carbonyl chloride 
• 6796-01-6 1-nitro-2-phenethylbenzene 
• 95-53-4 o-toluidine 
• 113-52-0 Imipramine hydrochloride 
• 13080-75-6 5-acetyliminodibenzyl 
• 50-49-7 impramine 
• 773837-37-9 sodium cyanide 
• 40583-89-9 5-propionyl-10,11-dihydro-5H-dibenzo[b,f]azepine 
• 91-40-7 2-(phenylamino)benzoic acid 
• 62-53-3 aniline 
• 108-86-1 bromobenzene 
• 21737-58-6 10,11-dihydro-5H-dibenzo[b,f]azepin-10-one 
• 1446358-22-0 2-(2-(N-phenyl-N-tosylamino)phenyl)acetic acid 

Downstream Products

• 64097-56-9 piperidinomethyl-2 dihydro-10,11 5H dibenzoazepine 
• 13080-72-3 N-benzyl-o,o'-iminodibenzyl 
• 739-71-9 trimipramine 
• 16036-79-6 5-(3-chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine 
• 16488-04-3 10,11-Dihydro-5-(3-dimethylaminopropionyl)-5H-dibenz azepin 
• 16488-05-4 N-(β-Diethylamino-propionyl)-iminodibenzyl 
• 19054-67-2 3-chloro-1-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propanone 
• 139156-15-3 methyl 3-(10,11-dihydro-5H-dibenz[b,f]azepin-5-ylmethyl)benzoate 
• 64097-57-0 N-methylpiperazinomethyl-2 dihydro-10,11 5H dibenzoazepine 
• 13080-75-6 5-acetyliminodibenzyl 
• 2095-95-6 didesmethylimipramine 
• 244196-39-2 5-(pyrrolidin-3-ylmethyl)-10,11-dihydro-5H-dibenzo[b,f]azepine 
• 1250431-00-5 (5H-dibenzo[b,f]azepin-5-yl)(4-phenylpiperazin-1-yl)methanone 
• 91222-34-3 4-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)benzaldehyde 

Relevant articles and documents

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Kinetics and thermodynamic parameters of the thermal decomposition of imipramine hydrochloride and trimipramine maleate

Thermal decomposition of imipramine hydrochloride and trimipramine maleate has been investigated isothermally and nonisothermally. The kinetic parameters, namely the activation energy Ea and the Arrhenius preexponential term A, were calculated. Applying the theory of activated complex to the process of decomposition one calculated ΔS≠, ΔH≠, and ΔG≠ for the reaction. The values of Ea as well as the thermodynamic functions did not vary significantly with temperature of the reaction whereas the preexponential term showed a significant dependence on the reaction temperature. Both imipramine hydrochloride and trimipramine maleate showed two main steps of decomposition. Each step proved to be a first-order reaction. The rate constant was calculated for each step, and the results were analyzed statistically.

Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores

The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.

Photo-catalytic preparation method of bibenzyl compounds

The invention relates to a preparation method of bibenzyl compounds. A compound represented by a formula (A) and a compound represented by a formula (C) carry out reactions under the action of an organic tungsten catalyst and an alkali in the presence of light to generate bibenzyl compounds represented by the formula (B). The method is simple and is easy to operate. The yield is high, and the application range is wide. Moreover, the invention also provides an application of a tungsten complex in organic chemical reactions as a photocatalyst.