62780-89-6

Basic information

• Product Name: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one
• Synonyms: 1-(3-Chloropropyl)-2-benzimidazolidinone,ca.90%,balance mainly bromo-derivative;1-(3-Chloropropyl)-2-benzimidazolidinone1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one;1-(3-Chloropropyl)-2-benzimidazolidinone, balance mainly bromo-derivative, ca. 90%;1-(3-Chloropropyl)-2-benziMidazolidinone, balance Mainly broMo-derivative, ca. 90% 50GR;1-(3-Chloropropyl)-1,3-dihydrobenziMidazol-2-one;3-(3-chloropropyl)-1H-benzimidazol-2-one;1-(3-chloropropyl)-1H-benzo[d]imidazol-2(3H)-one;1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-
• CAS NO: 62780-89-6
• Molecular Formula: C₁₀H₁₁ClN₂O
• Molecular Weight: 210.66
• EINECS: 263-731-6
• Product Categories: Aromatics;Heterocycles;Intermediates
• Mol File: 62780-89-6.mol

Chemical Properties

• Melting Point: 115-125 °C
• Appearance: White to slightly beige/Powder
• Density: 1.2798 (rough estimate)
• Vapor Pressure: 0.017Pa at 25℃
• Refractive Index: 1.5330 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 12.11±0.30(Predicted)
• Water Solubility: 210 mg/L (20 ºC)
• CAS DataBase Reference: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one(62780-89-6)
• EPA Substance Registry System: 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one(62780-89-6)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-41-37/38-25
• Safety Statements: 38-28A-45-39-26
• Hazardous Substances Data: 62780-89-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one is used as an intermediate in the synthesis of neuroleptic and antiallergic agents. Its unique chemical structure allows it to be a key component in the development of medications targeting neurological disorders and allergic reactions.
In the preparation of neuroleptic agents, 1-(3-Chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one contributes to the modulation of neurotransmitter activity, helping to alleviate symptoms associated with various mental health conditions.
For antiallergic applications, this benzimidazole derivative plays a role in the development of medications that can effectively reduce allergic responses, providing relief from symptoms such as itching, swelling, and inflammation.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H11ClN2O/c11-6-3-7-13-9-5-2-1-4-8(9)12-10(13)14/h1-2,4-5H,3,6-7H2,(H,12,14)

Synthetic route

1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one (62780-84-1) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
With phosphoric acid; propiononitrile at 75℃; for 4h; Concentration; Temperature;	92%
With hydrogenchloride In methanol; water at 20℃; Solvent; Reagent/catalyst;	90%
In hydrogenchloride; ethanol	9.5 parts (90%)

1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one (52099-72-6) + 1,3-chlorobromopropane (109-70-6) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
With sulfuric acid; sodium ethanolate 1) EtOH, reflux 4 h; 2) r.t., 2 h; Yield given. Multistep reaction;

(2-Amino-phenyl)-(3-chloro-propyl)-carbamic acid ethyl ester (100460-85-3) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
With calcium chloride at 210℃; for 1.5h; Yield given;

1-(3-chloropropyl)2-nitroaniline (62781-00-4) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: xylene / 18 h / Heating 2: H2 / 10percent Pd/C / methanol / 4 h 3: CaCl2 / 1.5 h / 210 °C View Scheme

(3-Chloro-propyl)-(2-nitro-phenyl)-carbamic acid ethyl ester (100460-82-0) → 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / 10percent Pd/C / methanol / 4 h 2: CaCl2 / 1.5 h / 210 °C View Scheme

1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) + methyl iodide (74-88-4) → 1-(3-chloropropyl)-1,3-dihydro-3-methyl-2H-benzimidazol-2-one (78056-57-2)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 20℃; for 1h;	98%
With sodium hydroxide In water; acetonitrile at 20℃; for 18h;	86%

5-ethyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol (36047-55-9) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (433261-68-8)

Conditions	Yield
Stage #1: 5-ethyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol With potassium hydroxide In water at 20℃; for 2h; Stage #2: 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one In water at 90℃; for 24h;	93.9%

formaldehyd (50-00-0) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-chloropropyl)-3-(hydroxymethyl)-1H-benzo[d]imidazol-2(3H)-one (1352949-10-0)

Conditions	Yield
With sodium acetate; acetic acid at 65℃; for 20h;	90%

1-(6,11-dihydrodibenzothiepin-11-yl)piperazine (121942-88-9) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(6,11-dihydrodibenzothiepin-11-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-94-7)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	83%

1-(8-chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yl)piperazine (23048-89-7) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(8-chloro-10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-04-2)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	76%

2-methyl-3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indole (84461-65-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(2-Methyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84461-66-5)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 18h; Heating;	76%

1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) + 1-(2-chloro-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-piperazine (52548-24-0) → 1-(3-(4-(2-chloro-10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-02-0)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	73%

1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) + 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (65347-55-9) → 1-{3-[4-(1H-Indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 18h; Heating;	69%

8-methylthio-10-piperazino-10,11-dihydrodibenzothiepin (27139-61-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(8-(methylthio)-10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-06-4)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	67%

1-(10,11-dihydrodibenzo[b,f]thiepin-10-yl)piperazine (4774-29-2) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(10,11-dihydrodibenzothiepin-10-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121943-00-8)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	65%

1-(2-methyl-6,11-dihydrodibenzothiepin-11-yl)piperazine (121942-90-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(2-methyl-6,11-dihydrodibenzothiepin-11-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-96-9)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	65%

diphenylmethylpiperazine (841-77-0) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → oxatomide (60607-34-3)

Conditions	Yield
With triethylamine; potassium iodide In toluene for 20h; Heating;	64%

3-(4-piperidinyl)-1H-indole (17403-09-7) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → N-{3-[4-(3-indolyl)-piperidino]-propyl}-benzimidazolone (97181-10-7)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 28h; Heating;	61%

1-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)piperazine (69159-50-8) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(10,11-dihydro-5H-dibenzocycloheptene-5-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-92-5)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	60%

4-propyloxypiperidine (88536-11-2) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-Butylpiperidine-1-yl)propyl)-1,3-dihydro-benzimidazol-2-one (509147-41-5)

Conditions	Yield
With potassium carbonate; sodium iodide	60%
With potassium carbonate; sodium iodide	60%

5-allyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol (247571-59-1) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (442653-38-5)

Conditions	Yield
Stage #1: 5-allyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol With potassium hydroxide In water at 20℃; for 2h; Stage #2: 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one In water at 90℃; for 24h;	55.2%

1-(2-ethoxyethyl)-2-(1-piperazinyl)-1H-benzimidazole (87233-69-0) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-<3-<4-<1-(2-ethoxyethyl)-1H-benzimidazol-2-yl>-1-piperazinyl>propyl>-1,3-dihydro-2H-benzimidazol-2-one (127533-18-0)

Conditions	Yield
With potassium carbonate In toluene for 14h; Heating;	53%

1-(4,9-dihydrothieno<2,3-c>-2-benzothiepin-4-yl)piperazine (121942-91-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(4-(4,9-dihydrothieno<2,3-c>-2-benzothiepin-4-yl)-1-piperazinyl)propyl)-1,3-dihydro-2H-benzimidazol-2-one (121942-98-1)

Conditions	Yield
With triethylamine; potassium iodide In toluene Heating;	50%

4-(indolyl-2)-piperidine + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 4-(indolyl-2)-1-benzimidazolonylpropyl-piperidine

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 18h; Heating;	49%

5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol (304003-33-6) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-(3-(5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one (1207874-69-8)

Conditions	Yield
Stage #1: 5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indole-3-thiol With potassium hydroxide In water at 20℃; for 2h; Stage #2: 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one In water at 90℃; for 24h;	47.6%

4-ethylpiperidin-4-ol (550369-44-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-[3-(4-Ethyl-4-hydroxypiperidin-1-yl)propyl]-1,3-dihydrobenzoimidazol-2-one

Conditions	Yield
With sodium carbonate; sodium iodide In acetonitrile for 4h; Heating / reflux;	43%

6-Methoxy-3-(4-piperidyl)-1,2-benzisoxazole hydrobromide (84163-17-7) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(6-Methoxy-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84243-01-6)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 16h;	37%

4-(5-fluoro-1,2-benzisoxazol-3-yl)piperidine hydrochloride (84163-16-6) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(5-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84242-99-9)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 8h;	36%

5,6-dimethoxy-3-(4-piperidyl)-1,2-benzisoxazole hydrobromide (84163-15-5) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(5,6-Dimethoxy-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84243-16-3)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 6h;	28%

6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride (84163-13-3) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(6-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (84243-00-5)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 12h;	27%

4-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (95742-20-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 4-fluoro-3-<1-<3-(1,3-dihydro-2-oxo-2H-benzimidazol-1-yl)propyl>-4-piperidinyl>-1,2-benzisoxazole (84243-18-5)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 90℃; for 6h;	26%

5-methoxy-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole (66611-26-5) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-{3-[4-(5-Methoxy-1H-indol-3-yl)-3,6-dihydro-2H-pyridin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one (97181-09-4)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide for 6h; Heating;	25%

3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (84163-22-4) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-[3-(4-Benzo[d]isoxazol-3-yl-piperidin-1-yl)-propyl]-1,3-dihydro-benzoimidazol-2-one (84231-49-2)

Conditions	Yield
With sodium carbonate; potassium iodide In various solvent(s) at 117℃; for 6h;	23%

4-Butyl-piperidin-4-ol (22093-38-5) + 1-(3-Chloropropyl)-1,3-dihydrobenzoimidazol-2-one (62780-89-6) → 1-[3-(4-Butyl-4-hydroxypiperidin-1-yl)propyl]-1,3-dihydrobenzoimidazol-2-one

Conditions	Yield
With sodium carbonate; sodium iodide In acetonitrile for 2h; Heating / reflux;	23%

Upstream product

• 52099-72-6 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one 
• 109-70-6 1.3-chlorobromopropane 
• 100460-85-3 (2-Amino-phenyl)-(3-chloro-propyl)-carbamic acid ethyl ester 
• 62781-00-4 1-(3-chloropropyl)2-nitroaniline 
• 100460-82-0 (3-Chloro-propyl)-(2-nitro-phenyl)-carbamic acid ethyl ester 
• 62780-84-1 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one 

Downstream Products

• 60607-34-3 oxatomide 
• 62781-57-1 1-{3-[4-(4-chloro-phenyl)-4-hydroxy-piperidin-1-yl]-propyl}-1,3-dihydro-benzoimidazol-2-one 
• 62781-08-2 8-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 
• 57808-66-9 domperidone 
• 62781-12-8 3-methyl-8-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one 
• 62781-13-9 1-(4-chloro-3-methyl-phenyl)-8-[3-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-propyl]-1,3,8-triaza-spiro[4.5]decan-4-one 
• 65214-93-9 1-[3-{4-[α-(4-fluorophenyl)-α-phenylmethyl]-1-piperazinyl}propyl]-1,3-dihydro-2H-benzimidazol-2-one 
• 1352949-08-6 tert-butyl 3-((8-(3-(3-(heptanoyloxymethyl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate 
• 359879-00-8 2-(4-methoxyphenyl)-N-(4-methylbenzyl)-N-(1-(3-(1,3-dihydro-2H-benzimidazol-2-one-1-yl)propyl)piperidine-4-yl) acetamide trifluoroacetate 

Relevant articles and documents

Method for synthesizing 1-(3-chloropropyl)-benzimidazole-2-ketone

The invention provides a method for synthesizing 1-(3-chloropropyl)-benzimidazole-2-ketone. The reaction route is shown in the description. The method has the beneficial effects that 1, the inventiondesigns the novel synthesis route to prepare a domperidone intermediate with the structure shown in the formula (DOM-4), and the novel synthesis route is realized; the reaction selectivity of the route is good, the controllability is strong, and the route is quite favorable for the implementation of large-scale industrial production; 2, by using the route and the method provided by the invention,the production cost of the domperidone intermediate is greatly lowered, and the purity of the domperidone intermediate is increased, so that the production cost of the domperidone intermediate is greatly reduced.

Synthesis method of domperidone drug intermediate 1-(3-chloropropyl)-benzimidazolyl-2-one

The invention relates to a synthesis method of a domperidone drug intermediate 1-(3-chloropropyl)-benzimidazolyl-2-one, which comprises the following steps: adding 0.19mol of 1-allylbenzoimidazolyl-2-one, 120-140ml of ethylene glycol and 0.26-0.28mol of sodium sulfite, heating to 35-40 DEG C, controlling the stirring rate at 110-130 rpm, dropwisely adding 0.23-0.25mol of 1-amido-3-bromo-propane within 2-3 hours, reacting for 4-5 hours, pouring the reaction product into a sodium chloride solution, extracting with cyclohexanol 5-7 times, drying the cyclohexanol extracting solution with calcium oxide, evaporating to remove the solvent to obtain oily 1-allyl-3-(3-chloropropyl)benzimidazolyl-2-one (3); and adding 120ml of phosphoric acid solution and 60ml of propionitrile into the oily product (3), controlling the stirring rate at 110-130 rpm, heating the solution to 70-75 DEG C, reacting for 3-4 hours, evaporating to remove partial propionitrile, cooling to precipitate a solid, filtering, washing the solid with salt solution, and dehydrating to obtain the 1-(3-chloropropyl)-benzimidazolyl-2-one.

2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS

The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent "chemoattractant receptor-homologous molecule expressed on Th2 cells" antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

TRICYCLIC ANALOGUES OF THE ANTIALLERGIC AGENT OXATOMIDE: 1-(3-(4-(10,11-DIHYDRO-5H-DIBENZOCYCLOHEPTENE-5-YL)-1-PIPERAZINYL)PROPYL)-1,3-DIHYDRO-2H-BENZIMIDAZOL-2-ONE AND THE RELATED 6,11-DIHYDRODIBENZOTHIEPIN, 4,9-DIHYDROTHIENO-2-BENZOTHIEPIN, AND ...

11-Chloro-6,11-dihydrodibenzothiepin and its 2-methyl derivative VI were transformed via the 11-(4-(ethoxycarbonyl)-1-piperazinyl) compounds IVc and Vc to 11-(1-piperazinyl) compounds IVb and Vb.Their reactions with 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one (II) afforded the title compounds IVa and IVb.Similar reactions and sequences in the series of 10,11-dihydro-5H-dibenzocycloheptene, 4,9-dihydrothieno-2-benzothiepin, and 10,11-dihydrodibenzothiepin led to further oxatomide (Ia) analogues IIIa and VIIa-XIa.In the test of passivecutaneous anaphylaxis in rats, compound VIIIa was more active than Ia, and IVa had similar activity like Ia.

A New Approach to 1-Alkyl-1,3-dihydro-2H-benzimidazol-2-ones

A new procedure for preparing 1-alkyl-1,3-dihydro-2H-benzimidazol-2-ones from o-nitroanilines by succesive ethoxycarbonylation, catalytic hydrogenation and thermal cyclization under neutral conditions is described. - (Keywords: Thermal cyclization)

1,3-Dihydro-1-[3-(1-piperidinyl)propyl]-2H-benzimidazol-2-ones and related compounds

Compounds of the class of 1-(benzazolyalkyl)piperidine derivatives useful as antiemetic agents.