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14028-44-5

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14028-44-5 Usage

Description

Amoxapine is a tetracyclic antidepressant with a wide range of pharmacological effects. It inhibits norepinephrine and serotonin reuptake, binding the respective transporters with Kd values of 16 and 58 nM. It has also been shown to act as either an antagonist or inverse agonist at serotonin 5-HT2A, 2B, 2C, 3, 6, 7 (Kis = 1 and 2 nM for 5-HT2A and 5-HT2C, respectively), dopamine D2, 3, 4 (Kd = 160 nM for D2), α1-adrenergic (Kd = 50 nM), and histamine H1 (Kd = 25 nM) receptors.

Chemical Properties

Crystalline Solid

Originator

Asendin,Lederle,US,1980

Uses

Different sources of media describe the Uses of 14028-44-5 differently. You can refer to the following data:
1. Amoxapine is intended more for relieving symptoms in patients with neurotic or situational depression. It has a number of serious side effects.
2. A tricyclic norepinephrine uptake inhibitor
3. antidepressant, inhibits norepinephrine uptake

Definition

ChEBI: A dibenzooxazepine compound having a chloro substituent at the 2-position and a piperazin-1-yl group at the 11-position.

Manufacturing Process

A mixture of 125 g of o-(p-chlorophenoxy)aniline hydrochloride and 100 ml of dry pyridine is treated cautiously with a solution of 90 ml of ethyl chlorocarbonate in 150 ml of ether. The mixture is kept at room temperature for 3 days, diluted with about 500 ml of water and extracted with 300 ml of ether, The ethereal extract is washed with 300 ml of water, dried over calcium chloride, filtered and concentrated. The resulting ethyl o-(pchlorophenoxy) carbanilate is obtained in a viscous oil suitable for use in the next step without further purification. A solution of 70 g of ethyl o-(p-chlorophenoxy)carbanilate and 120 g of Ncarbethoxypiperazine in 100 ml of benzene containing a little sodium methoxide is heated on a steam bath for about 5 days. The solvent is removed by distillation and the residue is triturated with water. The resulting solid is dissolved in ether and dried over sodium sulfate. Filtration and concentration then yields ethyl 4-[[o-(p-chlorophenoxy)phenyl]carbamoyl]-1- piperazinecarboxylate, melting at 89°C to 91°C, and suitable for cyclization. A mixture of 10 g of the above piperazine carboxylate ester, 8 g of phosphorus pentoxide and 20 ml of phosphorus oxychloride is heated under reflux for about 1 day, diluted with 100 ml each of chloroform and benzene and quenched with 200 g of ice. The mixture is made basic with 10% sodium hydroxide. The organic layer is isolated and extracted with 150 ml of dilute hydrochloric acid. The product is precipitated from the aqueous layer by addition of 10% sodium hydroxide, extracted with benzene and dried over potassium carbonate. Recrystallization from benzene-petroleum ether gives 2- chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine which melts at 175°C to 176°C.

Brand name

Asendin (Lederle).

Therapeutic Function

Antidepressant

General Description

Consideration of the structure of amoxapine, 2-chloro-11-(1-piperazinyl)dibenz-[b,f] [1,4]oxazepine (Asendin), reinforcesthe fact that many antidepressants are very closelyrelated to antipsychotics. Indeed, some, including amoxapine,have significant effects at D2 receptors. The Nmethyl–substituted relative of amoxapine is the antipsychoticloxapine (Loxitane). The 8-hydroxy metabolite ofamoxapine is reportedly active as an antidepressant and asa D2 receptor blocker.

Mechanism of action

Additionally, it is the N-desmethyl metabolite of the antipsychotic loxapine. Amoxapine differs structurally from the other secondary TCAs in that it has both a nitrogen and an oxygen atom in its 7-membered central ring and a piperazinyl ring rather than a propylamino side chain attached to the central ring.Amoxapine is a less potent inhibitor of neuronal NE reuptake compared with the other secondary TCAs, with a mechanism of action similar to that of desipramine.

Pharmacokinetics

Amoxapine shares the toxic potentials of the TCAs, and the usual precautions of TCA administration should be observed. Amoxapine resembles the atypical antipsychotic drugs in its intermediate affinity as an antagonist of dopamine-2 and of 5-HT2 receptors. Amoxapine is rapidly and almost completely absorbed from the gastrointestinal (GI) tract. Amoxapine and its 8-hydroxyamoxapine metabolite have been detected in human milk at concentrations below steady-state therapeutic concentrations.

Pharmacology

The antidepressant action of amoxapine is comparable to that of imipramine and amitriptyline. It exhibits antagonistic activity on dopamine (D2) receptors.

Clinical Use

Amoxapine is a dibenzoxazepine TCA with antidepressant and antipsychotic effects that has shown therapeutic effectiveness in patients with delusional depression.

Safety Profile

Poison by ingestion andintraperitoneal routes. Human systemic effects byingestion: acute renal failure, acute tubular necrosis, BPlowering, coma, convulsions, decreased body temperature,EKG changes, excitement, fasciculations, heart ratechanges, hype

Synthesis

Amoxapine, 2-chloro-11-(1-piperazinyl)-dibenz[b,f]oxazepine (7.3.2), is a direct analog of the neuroleptic loxapine (6.5.3), differing only in the absence of a methyl group in the piperazine region of the molecule. On the other hand, it could be included in the class of tricyclic antidepressants, the main difference being the presence of a side chain on the central 7-membered ring of the tricyclic system. Amoxapine, like loxapine, is synthesized from 2-(4-chlorobenzoxy)aniline, which as in loxapine synthesis is acidified with chlorocarbonic acid into (6.5.1) and further transformed into ureide (7.3.1) upon reaction with 1-carboethoxypiperazine. Cyclization by a mixture of phosphorous pentoxide and phosphorous oxychloride into the dibenzoxazepine and subsequent alkaline hydrolysis gives amoxapine (7.3.2) [50–53].

Metabolism

Amoxapine has the shortest elimination time (~8 hours) of the secondary TCAs. It is metabolized in the liver principally to 8-hydroxyamoxapine and to 7-hydroxyamoxapine. Both of these metabolites are pharmacologically active and have half-lives of 30 and 6.5 hours, respectively. The hydroxylation of amoxapine is inhibited by ketoconazole, suggesting the involvement of CYP3A4."

Check Digit Verification of cas no

The CAS Registry Mumber 14028-44-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,0,2 and 8 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 14028-44:
(7*1)+(6*4)+(5*0)+(4*2)+(3*8)+(2*4)+(1*4)=75
75 % 10 = 5
So 14028-44-5 is a valid CAS Registry Number.
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

14028-44-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (A2499)  Amoxapine  >97.0%(GC)(T)

  • 14028-44-5

  • 1g

  • 990.00CNY

  • Detail
  • TCI America

  • (A2499)  Amoxapine  >97.0%(GC)(T)

  • 14028-44-5

  • 5g

  • 3,390.00CNY

  • Detail
  • USP

  • (1031401)  Amoxapine  United States Pharmacopeia (USP) Reference Standard

  • 14028-44-5

  • 1031401-200MG

  • 4,647.24CNY

  • Detail
  • Sigma

  • (A129)  Amoxapine  

  • 14028-44-5

  • A129-100MG

  • 430.56CNY

  • Detail
  • Sigma

  • (A129)  Amoxapine  

  • 14028-44-5

  • A129-500MG

  • 1,698.84CNY

  • Detail
  • Sigma

  • (A129)  Amoxapine  

  • 14028-44-5

  • A129-5G

  • 8,090.55CNY

  • Detail

14028-44-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name amoxapine

1.2 Other means of identification

Product number -
Other names Moxadil

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14028-44-5 SDS

14028-44-5Synthetic route

piperazine
110-85-0

piperazine

2,11-dichloro-dibenzo[b,f][1,4]oxazepine
3455-14-9

2,11-dichloro-dibenzo[b,f][1,4]oxazepine

amoxapine
14028-44-5

amoxapine

Conditions
ConditionsYield
In xylene for 5h; Heating;
loxapine
1977-10-2

loxapine

amoxapine
14028-44-5

amoxapine

Conditions
ConditionsYield
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
3158-91-6

2-chlorodibenzo[b,f][1,4]oxazepin-11(10H)-one

amoxapine
14028-44-5

amoxapine

Conditions
ConditionsYield
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
148550-51-0

ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

amoxapine
14028-44-5

amoxapine

ethyl 2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)pyrimidine-5-carboxylate
1024010-80-7

ethyl 2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)pyrimidine-5-carboxylate

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 20℃; for 1h;100%
In 1,2-dimethoxyethane at 20℃; for 1h;100%
ethylenesulfonyl fluoride
677-25-8

ethylenesulfonyl fluoride

amoxapine
14028-44-5

amoxapine

2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)ethanesulfonyl fluoride

2-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)ethanesulfonyl fluoride

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
(4-ethynylphenyl)sulfurimidoyl difluoride

(4-ethynylphenyl)sulfurimidoyl difluoride

amoxapine
14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)-N-(4-ethynylphenyl)piperazine-1-sulfonimidoyl fluoride

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)-N-(4-ethynylphenyl)piperazine-1-sulfonimidoyl fluoride

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 20℃; for 2h;99%
amoxapine
14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-sulfonyl fluoride

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-sulfonyl fluoride

Conditions
ConditionsYield
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
811-68-7

silver(I) trifluoromethanethiolate

amoxapine
14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbothioyl fluoride

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbothioyl fluoride

Conditions
ConditionsYield
With potassium bromide In acetonitrile at 20℃; for 1h; Inert atmosphere;98%
With potassium bromide In acetonitrile at 25℃; for 1h;89%
trifluoromethyl trifluoromethanesulfonate
3582-05-6

trifluoromethyl trifluoromethanesulfonate

amoxapine
14028-44-5

amoxapine

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbonyl fluoride

4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazine-1-carbonyl fluoride

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.0833333h; Sealed tube;97%
methanol
67-56-1

methanol

amoxapine
14028-44-5

amoxapine

loxapine
1977-10-2

loxapine

Conditions
ConditionsYield
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%
deuteromethanol
1455-13-6

deuteromethanol

amoxapine
14028-44-5

amoxapine

C18H15(2)H3ClN3O

C18H15(2)H3ClN3O

Conditions
ConditionsYield
With aluminum (III) chloride; water-d2 In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;94%
allyl alcohol
107-18-6

allyl alcohol

amoxapine
14028-44-5

amoxapine

3-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)propan-1-ol

3-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)propan-1-ol

Conditions
ConditionsYield
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
58824-56-9

1-(p-bromophenyl)prop-2-en-1-ol

amoxapine
14028-44-5

amoxapine

(S)-1-(4-bromophenyl)-3-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)propan-1-ol

(S)-1-(4-bromophenyl)-3-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)propan-1-ol

Conditions
ConditionsYield
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%
deuteromethanol
1455-13-6

deuteromethanol

amoxapine
14028-44-5

amoxapine

C18H16(2)H2ClN3O

C18H16(2)H2ClN3O

Conditions
ConditionsYield
With aluminum (III) chloride In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;87%
1-methylindole
603-76-9

1-methylindole

amoxapine
14028-44-5

amoxapine

2-chloro-11-(4-(3-iodo-1-methyl-1H-indol-2-yl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

2-chloro-11-(4-(3-iodo-1-methyl-1H-indol-2-yl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

Conditions
ConditionsYield
With ammonium iodide In dimethyl sulfoxide; acetonitrile at 20℃; Electrochemical reaction; Green chemistry;87%
benzonitrile
100-47-0

benzonitrile

amoxapine
14028-44-5

amoxapine

C24H22ClN3O

C24H22ClN3O

Conditions
ConditionsYield
With borane-ammonia complex; C16H29Cl2CoN2P at 20℃; for 13h; Schlenk technique; Inert atmosphere; chemoselective reaction;86%
p-trifluoromethylphenyl bromide
402-43-7

p-trifluoromethylphenyl bromide

amoxapine
14028-44-5

amoxapine

2-chloro-11-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

2-chloro-11-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

Conditions
ConditionsYield
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%
deuteromethanol
1455-13-6

deuteromethanol

amoxapine
14028-44-5

amoxapine

C18H17(2)HClN3O

C18H17(2)HClN3O

Conditions
ConditionsYield
With aluminum (III) chloride; water-d2 In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;86%
2-oxo-4-phenylbutyric acid
710-11-2

2-oxo-4-phenylbutyric acid

amoxapine
14028-44-5

amoxapine

1-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)-3-phenylpropane-1-thione

1-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)-3-phenylpropane-1-thione

Conditions
ConditionsYield
With sulfur; 1-dodecylthiol In tetrahydrofuran at 20℃; for 2h; Sealed tube; chemoselective reaction;84%
N-(pivaloyloxy)pent-4-enamide

N-(pivaloyloxy)pent-4-enamide

amoxapine
14028-44-5

amoxapine

5-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)piperidin-2-one

5-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)piperidin-2-one

Conditions
ConditionsYield
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
1224597-90-3

quinolin-2-yl N,N,N’,N’-tetramethyldiamidophosphate

amoxapine
14028-44-5

amoxapine

2-(amoxapin-N-yl)quinoline

2-(amoxapin-N-yl)quinoline

Conditions
ConditionsYield
With TurboGrignard In tetrahydrofuran at 0 - 25℃; for 8h; Inert atmosphere;78%
2-methoxyethylamine
109-85-3

2-methoxyethylamine

amoxapine
14028-44-5

amoxapine

N-(2-methoxyethyl)-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepin-2-amine

N-(2-methoxyethyl)-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepin-2-amine

Conditions
ConditionsYield
With C47H70BrO4PPdSi; sodium t-butanolate In tetrahydrofuran at 20℃; Sealed tube; Inert atmosphere;74%
(1-methyl-1H-indol-5-yl)boronic acid

(1-methyl-1H-indol-5-yl)boronic acid

amoxapine
14028-44-5

amoxapine

2-chloro-11-(4-((1-methyl-1H-indol-5-yl)sulfonyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

2-chloro-11-(4-((1-methyl-1H-indol-5-yl)sulfonyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

Conditions
ConditionsYield
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
50986-83-9

4-fluorobenzenesulfinyl chloride

amoxapine
14028-44-5

amoxapine

2-chloro-11-(4-((4-fluorophenyl)sulfinyl)piperazin-1-yl)dibenzo-[b,f ][1,4]oxazepine

2-chloro-11-(4-((4-fluorophenyl)sulfinyl)piperazin-1-yl)dibenzo-[b,f ][1,4]oxazepine

Conditions
ConditionsYield
With triethylamine at 20℃; for 0.5h; Inert atmosphere;69%
4-(tert-butyl)-N-(quinolin-8-yl)benzamide
912896-78-7

4-(tert-butyl)-N-(quinolin-8-yl)benzamide

amoxapine
14028-44-5

amoxapine

4-(tert-butyl)-2-(8-chloro-piperazin-1-yl)dibenzo[b,f][1,4]-oxazepine-N-(quinolin-8-yl)benzamide

4-(tert-butyl)-2-(8-chloro-piperazin-1-yl)dibenzo[b,f][1,4]-oxazepine-N-(quinolin-8-yl)benzamide

Conditions
ConditionsYield
With copper diacetate; sodium acetate In acetonitrile for 12h; Electrochemical reaction;63%
1-iodo-3,4-dimethoxybenzene
5460-32-2

1-iodo-3,4-dimethoxybenzene

amoxapine
14028-44-5

amoxapine

2-chloro-11-(4-((3,4-dimethoxyphenyl)sulfonyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

2-chloro-11-(4-((3,4-dimethoxyphenyl)sulfonyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

Conditions
ConditionsYield
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%
(E)-N-([1,1'-biphenyl]-4-yl)-2,2,2-trifluoroacetimidoyl cyanide

(E)-N-([1,1'-biphenyl]-4-yl)-2,2,2-trifluoroacetimidoyl cyanide

amoxapine
14028-44-5

amoxapine

N-(1-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)-2,2,2-trifluoroethylidene)-[1,1'-biphenyl]-4-amine

N-(1-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)-2,2,2-trifluoroethylidene)-[1,1'-biphenyl]-4-amine

Conditions
ConditionsYield
With triethylamine In toluene at 120℃; for 12h; Inert atmosphere; Schlenk technique;61%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

amoxapine
14028-44-5

amoxapine

C24H19ClN4O

C24H19ClN4O

Conditions
ConditionsYield
With Pd(PAd3)(4-FC6H4)Br; triethylamine In water; toluene at 80℃; for 48h; Inert atmosphere; Glovebox; chemoselective reaction;61%
3,3-difluorocyclobutane-1-carbaldehyde
1246765-49-0

3,3-difluorocyclobutane-1-carbaldehyde

C16H19NO4

C16H19NO4

amoxapine
14028-44-5

amoxapine

C38H41ClF2N4O5

C38H41ClF2N4O5

Conditions
ConditionsYield
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%
4-methoxy-N-tritylbenzenesulfonimidoyl fluoride

4-methoxy-N-tritylbenzenesulfonimidoyl fluoride

amoxapine
14028-44-5

amoxapine

2-chloro-11-(4-(4-methoxy-N-tritylphenylsulfonimidoyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepane

2-chloro-11-(4-(4-methoxy-N-tritylphenylsulfonimidoyl)piperazin-1-yl)dibenzo[b,f][1,4]oxazepane

Conditions
ConditionsYield
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%
cyclobutanone O-perfluorobenzoyl oxime

cyclobutanone O-perfluorobenzoyl oxime

amoxapine
14028-44-5

amoxapine

4-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)butanenitrile

4-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)butanenitrile

Conditions
ConditionsYield
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%
tert-butyl (fluoro(methyl)(oxo)-λ6-sulfaneylidene)carbamate

tert-butyl (fluoro(methyl)(oxo)-λ6-sulfaneylidene)carbamate

amoxapine
14028-44-5

amoxapine

tert-butyl ((4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)(methyl)(oxo)-λ6-sulfaneylidene)carbamate

tert-butyl ((4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)(methyl)(oxo)-λ6-sulfaneylidene)carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 80℃; for 24h; Inert atmosphere;45%
carbon monoxide
201230-82-2

carbon monoxide

(S)-4-phenylbutan-2-yl 4-methylbenzenesulfonate
116199-39-4

(S)-4-phenylbutan-2-yl 4-methylbenzenesulfonate

amoxapine
14028-44-5

amoxapine

(R)-1-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)-2-methyl-4-phenylbutan-1-one

(R)-1-(4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-yl)piperazin-1-yl)-2-methyl-4-phenylbutan-1-one

Conditions
ConditionsYield
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%

14028-44-5Relevant articles and documents

PAINKILLING ASSOCIATION COMPRISING A DIHYDROIMIDAZOPYRAZINE DERIVATIVE

-

, (2009/10/31)

The invention relates to a product comprising (1R)-1-[(({2R)-2-amino-3-[(8S)-8-(cyclohexylmethyl) -2-phenyl-5,6-dihydroimidazo [1,2-a]pyrazin-7(8H)-yl]-3-oxopropyl}dithio)methyl]-2-[(8S)-8-(cyclohexylmethyl) -2-phenyl-5,6-dihydrolmidazo[1,2-a]pyrazin-7(8H)-yl]-2-oxoethylamine in association with an analgesic agent selected from morphine, the similar or a morphine derivative, sodium channel inhibitors, non-steroidal antiflammatory agents (AINS), glutamatergic system inhibitors, tricycle antidepressants and gabaergic derivatives for simultaneous therapeutic use which is separated or out over the time for pain treatment or prevention.

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