Conditions | Yield |
---|---|
In xylene for 5h; Heating; |
loxapine
amoxapine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. HCl / 16 h / Heating 2: POCl3, PhNMe2 / 5 h / Heating 3: xylene / 5 h / Heating View Scheme |
2-chlorodibenzo[b,f][1,4]oxazepin-11(10H)-one
amoxapine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: POCl3, PhNMe2 / 5 h / Heating 2: xylene / 5 h / Heating View Scheme |
ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate
amoxapine
ethyl 2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)pyrimidine-5-carboxylate
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane at 20℃; for 1h; | 100% |
In 1,2-dimethoxyethane at 20℃; for 1h; | 100% |
ethylenesulfonyl fluoride
amoxapine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 100% |
amoxapine
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide at 20℃; for 2h; | 99% |
amoxapine
Conditions | Yield |
---|---|
With dmap; potassium fluoride; N-ethyl-N,N-diisopropylamine; N,N`-sulfuryldiimidazole; trifluoroacetic acid In dichloromethane at 20℃; for 16h; | 99% |
With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; | 95% |
With 1-(fluorosulfuryl)-2,3-dimethyl-1H-imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; | 95% |
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.166667h; | 93% |
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; potassium carbonate In dimethyl sulfoxide at 20℃; for 1h; | 89% |
silver(I) trifluoromethanethiolate
amoxapine
Conditions | Yield |
---|---|
With potassium bromide In acetonitrile at 20℃; for 1h; Inert atmosphere; | 98% |
With potassium bromide In acetonitrile at 25℃; for 1h; | 89% |
trifluoromethyl trifluoromethanesulfonate
amoxapine
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.0833333h; Sealed tube; | 97% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation; | 95% |
With [(Cp*IrCl)2(4,4′,6,6′-tetrahydroxy-2,2′-bipyrimidine)][Cl]2; potassium hydroxide In water at 130℃; for 12h; Schlenk technique; | 73% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; water-d2 In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | 94% |
allyl alcohol
amoxapine
Conditions | Yield |
---|---|
With potassium phosphate; [(bis(2-dicyclohexylphosphinoethyl)amine)Fe(CO)Br2]; sodium triethylborohydride In cyclohexane at 80℃; for 24h; Inert atmosphere; Sealed tube; | 91% |
1-(p-bromophenyl)prop-2-en-1-ol
amoxapine
Conditions | Yield |
---|---|
With potassium phosphate; chloro{(R)-(+)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl}[(2R)-(-)-1-(4-methoxyphenyl)-1'-(4-methoxyphenyl-kC)-3-methyl-1,2-butanediamine]ruthenium(II) In toluene at 30℃; for 72h; Inert atmosphere; Sealed tube; enantioselective reaction; | 89% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | 87% |
1-methylindole
amoxapine
Conditions | Yield |
---|---|
With ammonium iodide In dimethyl sulfoxide; acetonitrile at 20℃; Electrochemical reaction; Green chemistry; | 87% |
Conditions | Yield |
---|---|
With borane-ammonia complex; C16H29Cl2CoN2P at 20℃; for 13h; Schlenk technique; Inert atmosphere; chemoselective reaction; | 86% |
p-trifluoromethylphenyl bromide
amoxapine
Conditions | Yield |
---|---|
With nickel(II) bromide dimethoxyethane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine; lithium bromide In 1,2-dimethoxyethane; N,N-dimethyl acetamide at 20℃; for 7h; Buchwald-Hartwig Coupling; Inert atmosphere; Electrochemical reaction; | 86% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; water-d2 In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | 86% |
2-oxo-4-phenylbutyric acid
amoxapine
Conditions | Yield |
---|---|
With sulfur; 1-dodecylthiol In tetrahydrofuran at 20℃; for 2h; Sealed tube; chemoselective reaction; | 84% |
amoxapine
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydrogencarbonate In 2,2,2-trifluoroethanol; water at 21℃; for 16h; regioselective reaction; | 79% |
quinolin-2-yl N,N,N’,N’-tetramethyldiamidophosphate
amoxapine
Conditions | Yield |
---|---|
With TurboGrignard In tetrahydrofuran at 0 - 25℃; for 8h; Inert atmosphere; | 78% |
2-methoxyethylamine
amoxapine
Conditions | Yield |
---|---|
With C47H70BrO4PPdSi; sodium t-butanolate In tetrahydrofuran at 20℃; Sealed tube; Inert atmosphere; | 74% |
amoxapine
Conditions | Yield |
---|---|
With 4,4'-Dimethoxy-2,2'-bipyridin; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; copper(II) bis(trifluoromethanesulfonate); caesium carbonate; dimethyl sulfoxide at 130℃; for 16h; Inert atmosphere; Sealed tube; | 71% |
4-fluorobenzenesulfinyl chloride
amoxapine
Conditions | Yield |
---|---|
With triethylamine at 20℃; for 0.5h; Inert atmosphere; | 69% |
4-(tert-butyl)-N-(quinolin-8-yl)benzamide
amoxapine
Conditions | Yield |
---|---|
With copper diacetate; sodium acetate In acetonitrile for 12h; Electrochemical reaction; | 63% |
1-iodo-3,4-dimethoxybenzene
amoxapine
Conditions | Yield |
---|---|
With dmap; 1-ethenyl-4-methylbenzene; palladium(II) acetylacetonate; 2,3,4,5-tetrabromothiophene 1,1-dioxide In dimethyl sulfoxide at 95℃; for 24h; Sealed tube; Inert atmosphere; | 62% |
amoxapine
Conditions | Yield |
---|---|
With triethylamine In toluene at 120℃; for 12h; Inert atmosphere; Schlenk technique; | 61% |
Conditions | Yield |
---|---|
With Pd(PAd3)(4-FC6H4)Br; triethylamine In water; toluene at 80℃; for 48h; Inert atmosphere; Glovebox; chemoselective reaction; | 61% |
Conditions | Yield |
---|---|
With tris[2-phenylpyridinato-C2,N]iridium(III); diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; propionic acid In dichloromethane at 20℃; for 2h; Molecular sieve; Irradiation; | 55% |
amoxapine
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-N-tritylbenzenesulfonimidoyl fluoride With aluminum (III) chloride In acetonitrile at 0℃; for 0.5h; Inert atmosphere; Sealed tube; Stage #2: amoxapine With triethylamine In acetonitrile at 0 - 20℃; for 16h; Inert atmosphere; Sealed tube; | 53% |
amoxapine
Conditions | Yield |
---|---|
With 2,6-bis[(4S)-4-methyl-4,5-dihydrooxazol-2-yl]pyridine; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Sealed tube; Inert atmosphere; Irradiation; | 45% |
amoxapine
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere; | 45% |
carbon monoxide
(S)-4-phenylbutan-2-yl 4-methylbenzenesulfonate
amoxapine
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine; dicobalt octacarbonyl In tert-Amyl alcohol at 70℃; under 30402 Torr; for 24h; Inert atmosphere; Sealed tube; | 43% |
The Amoxapine, with the CAS registry number 14028-44-5 and EINECS registry number 237-867-1, has the systematic name of 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine. It is a kind of crystalline solid, and belongs to the following product categories: Intermediates & Fine Chemicals; Pharmaceuticals; Adrenoceptor. It is a strong norepinephrine reuptake inhibitor and weak serotonin reuptake inhibitor. It also possesses antiadrenergic, anticholinergic, antidopaminergic, antihistamine, and antiserotonergic actions. The molecular formula of this chemical is C17H16ClN3O.
The physical properties of Amoxapine are as following: (1)ACD/LogP: 2.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.06; (4)ACD/LogD (pH 7.4): 1.76; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 9.32; (7)ACD/KOC (pH 5.5): 2.32; (8)ACD/KOC (pH 7.4): 117.52; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 28.07 Å2; (13)Index of Refraction: 1.685; (14)Molar Refractivity: 86.74 cm3; (15)Molar Volume: 228.2 cm3; (16)Polarizability: 34.39×10-24cm3; (17)Surface Tension: 52.1 dyne/cm; (18)Density: 1.37 g/cm3; (19)Flash Point: 238 °C; (20)Enthalpy of Vaporization: 73.23 kJ/mol; (21)Boiling Point: 469.9 °C at 760 mmHg; (22)Vapour Pressure: 5.32E-09 mmHg at 25°C.
Preparation and uses of Amoxapine: o-(p-chlorophenoxy) benzene Ethyl carbamate react with N-ethyl piperazine-based to give 4-[[o-(p-chlorophenoxy)phenyl]carbamoyl]-1-piperazine carboxylate. Then heat it with phosphorus pentoxide and phosphorus oxychloride to reflux. And you can get the aim product with this cyclization reaction. What's more, Amoxapine is used in the treatment of depression, anxiety disorders, panic disorder, and bipolar disorder.
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: Clc2ccc1Oc4c(/N=C(\c1c2)N3CCNCC3)cccc4
(2)InChI: InChI=1/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2
(3)InChIKey: QWGDMFLQWFTERH-UHFFFAOYAA
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD | unreported | > 20mg/kg (20mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: IRRITABILITY | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979. |
child | LDLo | oral | 25mg/kg (25mg/kg) | SENSE ORGANS AND SPECIAL SENSES: MIOSIS (PUPILLARY CONSTRICTION): EYE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Southern Medical Journal. Vol. 76, Pg. 543, 1983. |
child | TDLo | oral | 10mg/kg (10mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP | JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983. |
dog | LD | unreported | > 20mg/kg (20mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: IRRITABILITY | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979. |
dog | LDLo | intraperitoneal | 20mg/kg (20mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979. |
man | TDLo | oral | 4285ug/kg/2D- (4.285mg/kg) | BEHAVIORAL: EXCITEMENT | American Journal of Psychiatry. Vol. 140, Pg. 115, 1983. |
man | TDLo | oral | 4286ug/kg (4.286mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: REGIDITY | Southern Medical Journal. Vol. 77, Pg. 94, 1984. |
man | TDLo | oral | 14mg/kg (14mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | JAMA, Journal of the American Medical Association. Vol. 248, Pg. 3141, 1982. |
man | TDLo | oral | 27mg/kg (27mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Pharmacotherapy Vol. 15, Pg. 528, 1995. |
man | TDLo | oral | 70mg/kg/3W-I (70mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Journal of Clinical Psychiatry. Vol. 45, Pg. 358, 1984. |
man | TDLo | unreported | 5714ug/kg/2D- (5.714mg/kg) | PERIPHERAL NERVE AND SENSATION: FASCICULATIONS BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Southern Medical Journal. Vol. 76, Pg. 1077, 1983. |
monkey | LD | unreported | > 20mg/kg (20mg/kg) | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979. | |
mouse | LD50 | intraperitoneal | 112mg/kg (112mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: REGIDITY | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 233, Pg. 107, 1978. |
mouse | LD50 | oral | 104mg/kg (104mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 1, 1979. |
mouse | LD50 | subcutaneous | 385mg/kg (385mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971. |
rat | LD50 | intraperitoneal | 201mg/kg (201mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: REGIDITY BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 233, Pg. 107, 1978. |
rat | LD50 | oral | 313mg/kg (313mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971. |
rat | LD50 | subcutaneous | > 4500mg/kg (4500mg/kg) | Kiso to Rinsho. Clinical Report. Vol. 5, Pg. 1852, 1971. | |
women | LDLo | oral | 40mg/kg (40mg/kg) | CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE CARDIAC: CHANGE IN RATE CARDIAC: OTHER CHANGES | Annals of Emergency Medicine. Vol. 17, Pg. 274, 1988. |
women | LDLo | oral | 40mg/kg (40mg/kg) | BEHAVIORAL: COMA CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983. |
women | LDLo | oral | 75953ug/kg (75.953mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) CARDIAC: OTHER CHANGES CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Forensic Science International. Vol. 26, Pg. 33, 1984. |
women | TDLo | oral | 5mg/kg (5mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | JAMA, Journal of the American Medical Association. Vol. 250, Pg. 1069, 1983. |
women | TDLo | oral | 15mg/kg/5D-I (15mg/kg) | ENDOCRINE: HYPERGLYCEMIA | Journal of Clinical Psychiatry. Vol. 44, Pg. 347, 1983. |
women | TDLo | oral | 17mg/kg (17mg/kg) | BEHAVIORAL: COMA VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 101, 1983. |
women | TDLo | oral | 30mg/kg (30mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE | JAMA, Journal of the American Medical Association. Vol. 248, Pg. 1092, 1982. |
women | TDLo | oral | 50mg/kg (50mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA | Ugeskrift for Laeger. Doctor's Weekly. Vol. 146, Pg. 3285, 1984. |
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