N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride
ticlopidine hydrochloride
Conditions | Yield |
---|---|
In 1,3-DIOXOLANE; ethyl acetate | 95% |
With hydrogenchloride In 1,3-dioxane; water at 90℃; for 6h; Temperature; | 82% |
1,3-DIOXOLANE
N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride
ticlopidine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride | 89% |
With hydrogenchloride In water at 90℃; for 6h; Temperature; | 82% |
With hydrogenchloride In water at 90℃; for 6h; Temperature; | 91 g |
4,5,6,7-tetrahydrothieno[3,2-c]pyridine
1-chloro-2-(chloromethyl)benzene
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Stage #1: 4,5,6,7-tetrahydrothieno[3,2-c]pyridine; 1-chloro-2-(chloromethyl)benzene In dichloromethane at 60℃; for 1h; Stage #2: With hydrogenchloride In dichloromethane Reagent/catalyst; Solvent; Temperature; | 87% |
[2-(2-thyenyl)ethyl]amine
methyleneamine
1-chloro-2-(chloromethyl)benzene
ticlopidine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; formaldehyd; potassium carbonate In tetrahydrofuran; methanol; water; toluene | 84% |
4,5,6,7-tetrahydrothieno[3,2-c]pyridine
di-isopropyl ether
1-chloro-2-(chloromethyl)benzene
ticlopidine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydrogencarbonate In ethanol | 83% |
ticlopidine hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In 1,3-dioxane; water at 90℃; for 6h; Temperature; | 82% |
pyrographite
N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride With hydrogenchloride In 1,3-dioxane; water at 7 - 90℃; for 9h; Stage #2: pyrographite In ethanol at 4℃; for 4h; Temperature; | 82% |
Chloromethyl pivalate
N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine
ticlopidine hydrochloride
Conditions | Yield |
---|---|
In dimethyl sulfoxide | 51% |
1,3 dithiane
N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine hydrochloride
ticlopidine hydrochloride
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane | 9.4 g (62.7%) |
N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine
ticlopidine hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide; methanesulfonic acid; paraformaldehyde In N-methyl-acetamide; dichloromethane |
[2-(2-thyenyl)ethyl]amine
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / methanol / 2 h / Reflux 2: sodium tetrahydroborate / methanol / 0 - 20 °C 3: N,N-dimethyl-formamide / 0 - 60 °C View Scheme |
N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine
chloromethyl methyl ether
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Stage #1: N-(2-chloro-benzyl)-2-(thien-2-yl)-ethylamine; chloromethyl methyl ether In N,N-dimethyl-formamide at 0 - 60℃; Stage #2: With hydrogenchloride In ethanol |
2-chloro-benzaldehyde
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / methanol / 2 h / Reflux 2: sodium tetrahydroborate / methanol / 0 - 20 °C 3: N,N-dimethyl-formamide / 0 - 60 °C View Scheme |
C13H12ClNS
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0 - 20 °C 2: N,N-dimethyl-formamide / 0 - 60 °C View Scheme |
2-thiophenethanol
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / toluene / 3.5 h / 0 - 20 °C 2.1: toluene / 3 h / 85 °C 2.2: 4 h / 2 °C / pH 5 - 8.5 3.1: hydrogenchloride / water; 1,3-dioxane / 6 h / 90 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / toluene / 3.5 h / 0 - 20 °C 2.1: toluene / 3 h / 85 °C 2.2: 1 h / 20 °C / pH 8.5 3.1: hydrogenchloride / water; 1,3-dioxane / 6 h / 90 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 3 h / 0 - 20 °C 2.1: toluene / 4 h / 20 - 85 °C 2.2: pH 8.5 3.1: hydrogenchloride / water; 1,3-dioxane / 9 h / 7 - 90 °C 3.2: 4 h / 4 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / toluene / 3.5 h / 0 - 20 °C 2.1: toluene / 3 h / 85 °C 2.2: 4 h / 2 °C / pH 5 - 8.5 3.1: hydrogenchloride / water / 6 h / 90 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 3.5 h / 0 - 25 °C 2.1: toluene / 4 h / 25 - 90 °C 2.2: 4 h / 2 °C / pH 5 3.1: hydrogenchloride / water / 6 h / 90 °C View Scheme |
ticlopidine hydrochloride
Conditions | Yield |
---|---|
Stage #1: ticlopidine hydrochloride With sodium hydrogencarbonate In water Inert atmosphere; Stage #2: 4-(3-(pyridin-2-ylthio)propyl)morpholine With bis(1,5-cyclooctadiene)nickel (0); 3,4-thiene-2,3-diylbis(dicyclohexylphosphine); zinc In toluene at 150℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; | 76% |
The Ticlopidine hydrochloride, with the CAS registry number 53885-35-1 and EINECS registry number 258-837-4, has the systematic name of 5-(2-chlorobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (1:1). It is a kind of white solid, and belongs to the following product categories: Active Pharmaceutical Ingredients; Heterocyclic Compounds; Bases & Related Reagents; Heterocycles; Intermediates & Fine Chemicals; Nucleotides; Pharmaceuticals; Sulfur & Selenium Compounds; API's; Purinergics P2 receptor. And the molecular formula of this chemical is C14H14ClNS.HCl. What's more, it is often used as antiplatelet drug.
Physical properties about Ticlopidine hydrochloride are: (1)ACD/LogP: 3.231; (2)ACD/LogD (pH 5.5): 1.64; (3)ACD/LogD (pH 7.4): 3.06; (4)ACD/BCF (pH 5.5): 4.28; (5)ACD/BCF (pH 7.4): 112.21; (6)ACD/KOC (pH 5.5): 34.69 ; (7)ACD/KOC (pH 7.4): 910.40; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.638; (11)Molar Refractivity: 74.44 cm3; (12)Molar Volume: 207.057 cm3; (13)Polarizability: 29.51 10-24cm3; (14)Surface Tension: 51.5359992980957 dyne/cm; (15)Density: 1.274 g/cm3; (16)Flash Point: 175.918 °C; (17)Enthalpy of Vaporization: 61.378 kJ/mol; (18)Boiling Point: 367.268 °C at 760 mmHg
Preparation of Ticlopidine hydrochloride: Add 4,5,6,7-tetrahydro thieno [3,2-c] pyridine 13.9g(0.1mol), 2-chlorobenzyl chloride 16.1g (0.1mol), triethylamine 15g(0.15mol) and acetonitrile 150ml to the reaction bulb at room temperature with stirring, recycle the acetonitrile by vacuum concentration. Add 100ml toluene and 100ml water, and the solution should be fully mixed, then the solution will separate if left to stand. Get the toluene layer, and dry it with MgSO4. After filtering, control the PH to 2 by adding chlorine hydride isopropyl alcohol solution, and keep stirring for 2 minutes, cool it down, and separate out solid. Filter again, and gives pale yellow sokid. Recrystallize with absolute ethyl alcohol, you can get the white solid, and that's your aim product. The yield is about 75%.
You should be cautious while dealing with this chemical. It is harmful if swallowed. Therefore, you had better take the wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: Cl.Clc1ccccc1CN3Cc2c(scc2)CC3
(2)InChI: InChI=1/C14H14ClNS.ClH/c15-13-4-2-1-3-11(13)9-16-7-5-14-12(10-16)6-8-17-14;/h1-4,6,8H,5,7,9-10H2;1H
(3)InChIKey: MTKNGOHFNXIVOS-UHFFFAOYAY
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
monkey | LD50 | intraperitoneal | 500mg/kg (500mg/kg) | New Drugs Annual: Cardiovascular Drugs. Vol. 1, Pg. 295, 1983. | |
mouse | LD50 | intravenous | 55mg/kg (55mg/kg) | United States Patent Document. Vol. #4051141, | |
mouse | LD50 | oral | 600mg/kg (600mg/kg) | Medical Pharmacy. Vol. 15, Pg. 272, 1981. | |
mouse | LD50 | subcutaneous | 2690mg/kg (2690mg/kg) | Medical Pharmacy. Vol. 15, Pg. 272, 1981. | |
rat | LD50 | intravenous | 70mg/kg (70mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1204, 1981. | |
rat | LD50 | oral | 1780mg/kg (1780mg/kg) | Medical Pharmacy. Vol. 15, Pg. 272, 1981. | |
rat | LD50 | subcutaneous | > 3gm/kg (3000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Yakkyoku. Pharmacy. Vol. 32, Pg. 1499, 1981. |
women | LDLo | unreported | 180mg/kg/18D- (180mg/kg) | BLOOD: APLASTIC ANEMIA LIVER: LIVER FUNCTION TESTS IMPAIRED SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Journal of Hematology. Vol. 59, Pg. 260, 1998. |
women | TDLo | oral | 49mg/kg/1W-I (49mg/kg) | LIVER: LIVER FUNCTION TESTS IMPAIRED LIVER: "JAUNDICE, CHOLESTATIC" | American Journal of Hospital Pharmacy. Vol. 51, Pg. 1821, 1994. |
women | TDLo | oral | 189mg/kg/17D- (189mg/kg) | LIVER: "JAUNDICE, CHOLESTATIC" LIVER: LIVER FUNCTION TESTS IMPAIRED | American Journal of Hospital Pharmacy. Vol. 51, Pg. 1821, 1994. |
women | TDLo | oral | 1896mg/kg/26W (1896mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: "JAUNDICE, CHOLESTATIC" | Clinical Pharmacy. Vol. 12, Pg. 398, 1993. |
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