494-19-9

Usage

Uses

Used in Pharmaceutical Industry:
Iminodibenzyl is used as a drug intermediate for the synthesis of medications targeting tristimania and epilepsia due to its tricyclic ring structure, which is similar to that of phenothiazines.
Used in Analytical Applications:
Iminodibenzyl, specifically its metabolite 10,11-Dihydro-5H-dibenzo[b,f]azepine, is used as a chromogenic probe for the quantification of hydrogen peroxide and glucose. This makes it suitable for several analytical applications, including but not limited to:
1. Pharma Release Testing: Iminodibenzyl serves as a secondary standard for quality control in pharmaceutical laboratories and manufacturers, providing a convenient and cost-effective alternative to in-house working standards.
2. Pharma Method Development: It is utilized for qualitative and quantitative analyses in the development of pharmaceutical methods.
3. Food and Beverage Quality Control Testing: Iminodibenzyl is employed in the quality control testing of the food and beverage industry, ensuring the safety and quality of products.
4. Other Calibration Requirements: Iminodibenzyl is also used for various other calibration requirements in different industries, contributing to the accuracy and reliability of measurements and analyses.

Preparation

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

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 
• 113-52-0 Imipramine hydrochloride 
• 152700-41-9 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 
• 95-53-4 o-toluidine 
• 34124-14-6 2,2'-ethylenedianiline 
• 64-19-7 acetic acid 
• 16968-19-7 2,2'-dinitrobibenzyl 
• 88-72-2 1-methyl-2-nitrobenzene 
• 13080-75-6 5-acetyliminodibenzyl 
• 329060-91-5 C₂₂H₁₉NO₂ 
• 23868-11-3 ethyl 2-(phenylamino)benzoate 
• 53044-24-9 N-Phenyl-o-(hydroxymethyl)aniline 

Downstream Products

• 33948-19-5 10,11-dihydro-dibenzo[b,f]azepine-5-carbonyl chloride 
• 3534-05-2 5-chloroacetyl-10,11-dihydro-5H-dibenzazepine 
• 50-49-7 impramine 
• 2095-90-1 5-(2-Diethylaminoethyl)-iminodibenzyl 
• 64097-58-1 morpholinomethyl-2 dihydro-10,11 5H dibenzoazepine 
• 64097-61-6 bis(morpholinomethyl)-2,8 dihydro-10,11 5H dibenzoazepine 
• 64097-59-2 pyrrolydinomethyl-2 dihydro-10,11 5H dibenzoazepine 
• 64097-56-9 piperidinomethyl-2 dihydro-10,11 5H dibenzoazepine 
• 64097-57-0 N-methylpiperazinomethyl-2 dihydro-10,11 5H dibenzoazepine 
• 4513-01-3 10,11-dihydro-5-methyl-5H-dibenz[b,f]azepine 
• 78943-60-9 10,11-dihydro-N-phenyldibenzazepine 
• 88482-76-2 5-(o-Chloromethylbenzoyl)-10,11-dihydro-5H-dibenzazepine 
• 88482-77-3 5-(m-Chloromethylbenzoyl)-10,11-dihydro-5H-dibenzazepine 
• 13080-72-3 N-benzyl-o,o'-iminodibenzyl 

Relevant academic research and scientific papers

In vitro studies of dna damage caused by tricyclic antidepressants: A role of peroxidase in the side effects of the drugs

Studies show that tricyclic antidepressants prescribed for migraines, anxiety, and child enuresis have numerous adverse effects in living cells. One of the undesired outcomes observed under treatment with these drugs is DNA damage. However, the mechanisms underlying damage have yet to be elucidated. We performed in vitro studies of the DNA damage caused by four tricyclic antidepressants: imipramine, amitriptyline, opipramol, and protriptyline. We focused particularly on the DNA damage aided by peroxidases. As a model of a peroxidase, we used horseradish peroxidase (HRP). At pH 7, reactions of HRP with excess hydrogen peroxide and imipramine yielded an intense purple color and a broad absorption spectrum with the maximum intensity at 522 nm. Reactions performed between DNA and imipramine in the presence of H2O 2 and HRP resulted in the disappearance of the DNA band. In the case of the other three drugs, this effect was not observed. Extraction of the DNA from the reaction mixture indicated that DNA is degraded in the reaction between imipramine and H2O2 catalyzed by HRP. The final product of imipramine oxidation was identified as iminodibenzyl. We hypothesize that the damage to DNA was caused by an imipramine reactive intermediate.

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.

Iron-Catalyzed α-C-H Cyanation of Simple and Complex Tertiary Amines

This manuscript details the development of a general and mild protocol for the α-C-H cyanation of tertiary amines and its application in late-stage functionalization. Suitable substrates include tertiary aliphatic, benzylic, and aniline-type substrates and complex substrates. Functional groups tolerated under the reaction conditions include various heterocycles and ketones, amides, olefins, and alkynes. This broad substrate scope is remarkable, as comparable reaction protocols for α-C-H cyanation frequently occur via free radical mechanisms and are thus fundamentally limited in their functional group tolerance. In contrast, the presented catalyst system tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway. All components of the described catalyst system are readily available, allowing implementation of the presented methodology without the need for lengthy catalyst synthesis.

Synthesis method of iminodibenzyl

The invention relates to the field of drug intermediate synthesis, in particular to a synthesis method of iminodibenzyl, which mainly comprises two steps: a reduction reaction and a cyclization reaction. The yield can be improved to 88%-92% through fine control of the reduction reaction and the cyclization reaction, and the synthesis method has great industrial significance and is worthy of further popularization.

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.

Preparation method of imino-adenine intermediate and derivative thereof

The invention provides a preparation method of imino intermediate dihydro-5H-dibenzo [b, f] azepine. The adopted reaction substrates are 2-bromo-benzoyl chloride, aniline and triethylamine, and the dihydro-5H-dibenzo [b, f] azepine is prepared by a one-step method under a catalytic system of cuprous iodide. The invention further discloses a dihydro-5H-dibenzo [b, f] azepine derivative prepared bythe preparation method. The reaction overcomes the defects of lengthy preparation process, high cost, long consumed time and low yield in the traditional method; a one-step reaction is conducted to obtain the intermediate dihydro-5H-dibenzo [b, f] azepine and the derivative thereof, the yield of the target product is as high as 45-55%, the preparation route of the dihydro-5H-dibenzo [b, f] azepineis greatly shortened, the preparation effect of the dihydro-5H-dibenzo [b, f] azepine is improved, and the method has a wide industrial prospect.

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.

Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane

The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.

Photoredox-Catalyzed Cα-H Cyanation of Unactivated Secondary and Tertiary Aliphatic Amines: Late-Stage Functionalization and Mechanistic Studies

This paper describes the development and mechanistic studies of a general, high-yielding amine Cα-H cyanation protocol via photoredox catalysis. Inexpensive NaCN is employed as the cyanide source and air is the external oxidant, resulting in mild and highly functional group tolerant conditions. Notably, efficient Cα-H cyanations of secondary and tertiary aliphatic amines and of complex, biologically active compounds (drugs) can be performed using the established methodology. Mechanistic studies suggest that the carboxylic acid additive has three effects: formation of a stabilizing hemiaminal intermediate, prevention of catalyst decomposition by protonating the substrate, and modulation of fluorescence quenching of the photoexcited catalyst species.

Method for preparing medicine and medicine intermediate by continuous solid-liquid-gas three-phase reaction

The invention provides a method for preparing meropenem or a 10,11-dihydro-5H-dibenzo[b, f] azepine by a continuous solid-liquid-gas three-phase reaction. A reactant in which acatalyst is dissolved ispumped into a microchannel reactor by using a diaphragm pump, and the hydrogen is bubbled into the reactor by using the pressure of a steel cylinder. The method uses the microchannel reactor to realize the continuous production of the meropenem or the 10,11-dihydro-5H-dibenzo[b, f] azepine. The technical effects of short reaction time, thorough reaction and high product yield are achieved.