3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5 H-dibenzazepine HCl

Base Information

• Chemical Name: 3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5 H-dibenzazepine HCl
• CAS No.: 17321-77-6
• Molecular Formula: C19H23ClN2.HCl
• Molecular Weight: 351.319
• Hs Code.: 2933996100
• Mol file: 17321-77-6.mol

Synonyms:AKOS026749844;3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5 H-dibenzazepine HCl

Chemical Property of 3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5 H-dibenzazepine HCl

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 9.63E-08mmHg at 25°C
• Melting Point: 189-190 °C
• Boiling Point: 434.2 °C at 760 mmHg
• Flash Point: 216.4 °C
• PSA: 6.48000
• LogP: 5.39540
• Storage Temp.: Store at RT
• Solubility.: H2O: 25 mg/mL
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 350.1316542
• Heavy Atom Count: 23
• Complexity: 346

Purity/Quality:

99.5% ^*data from raw suppliers

Clomipramine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 20/21/22-39/23/24/25-23/24/25-11-36/37/38
• Safety Statements: 36-45-36/37-16-7-62-38-36/37/39-28-26-24/25-22-20/21-13

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [H+].CN(C)CCCN1C2=CC=CC=C2CCC3=C1C=C(C=C3)Cl.[Cl-]
• Description: Clomipramine is a tricyclic antidepressant, the 3-chlorinated derivative of imipramine . Like imipramine, clomipramine potently inhibits serotonin and norepinephrine reuptake (Kis = 7.4 and 96 nM, respectively). It also is an antagonist at histamine, muscarinic acetylcholine, α1-adrenergic, and dopamine receptors (Kds = 31, 37, 38, and 190 nM for H1, M1, α1, and D2, respectively).
• Uses: Potent, selective 5-HT uptake blocker Serotonin reuptake inhibitor. Antidepressant; antiobsessional agent anti-depressant, serotonin uptake inhibitor
• Therapeutic Function: Antidepressant
• Clinical Use: #N/A
• Drug interactions: Potentially hazardous interactions with other drugs Alcohol: increased sedative effect. Analgesics: increased risk of CNS toxicity with tramadol; possibly increased risk of side effects with nefopam; possibly increased sedative effects with opioids. Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone - avoid; increased risk of ventricular arrhythmias with disopyramide, flecainide or propafenone; avoid with dronedarone. Antibacterials: increased risk of ventricular arrhythmias with delamanid and moxifloxacin and possibly telithromycin - avoid with delamanid and moxifloxacin. Anticoagulants: may alter anticoagulant effect of coumarins. Antidepressants: possibly increased serotonergic effects with duloxetine; enhanced CNS excitation and hypertension with MAOIs and moclobemide; concentration possibly increased with SSRIs; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; possible increased risk of convulsions with vortioxetine. Antiepileptics: convulsive threshold lowered; concentration reduced by carbamazepine, phenobarbital and possibly fosphenytoin, phenytoin and primidone. Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol. Antipsychotics: increased risk of ventricular arrhythmias especially with droperidol, fluphenazine, haloperidol, pimozide, sulpiride and zuclopenthixol - avoid; increased risk of ventricular arrhythmias with risperidone; increased antimuscarinic effects with clozapine and phenothiazines; concentration increased by antipsychotics.Antivirals: increased risk of ventricular arrhythmias with saquinavir - avoid; concentration possibly increased with ritonavir. Atomoxetine: increased risk of ventricular arrhythmias and possibly convulsions. Beta-blockers: increased risk of ventricular arrhythmias with sotalol. Clonidine: tricyclics antagonise hypotensive effect; increased risk of hypertension on clonidine withdrawal. Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide. Dapoxetine: possibly increased risk of serotonergic effects - avoid. Dopaminergics: avoid use with entacapone; CNS toxicity reported with selegiline and rasagiline. Methylthioninium: risk of CNS toxicity - avoid if possible.

Technology Process of 3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5 H-dibenzazepine HCl

There total 3 articles about 3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5 H-dibenzazepine HCl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine (32943-25-2) + 3-dimethylaminopropionic acid (6300-04-5) → clomipramine hydrochloride (17321-77-6)

Guidance literature:

3-dimethylaminopropionic acid; With sodium tetrahydroborate; In toluene; at 0 - 5 ℃;

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine; With sodium tetrahydroborate; In toluene; at 25 - 80 ℃; for 5h;

With hydrogenchloride; In water; isopropyl alcohol;

DOI:10.1080/00397911.2017.1396613

Reference yield:

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine (32943-25-2) + 3-(Dimethylamino)propyl chloride (109-54-6) → clomipramine hydrochloride (17321-77-6)

Guidance literature:

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine; With potassium carbonate; potassium hydroxide; at 110 - 115 ℃; for 2h;

3-(Dimethylamino)propyl chloride; In toluene; at 110 - 115 ℃;

With hydrogenchloride; In acetone; at 2 ℃; for 8h; pH=2 - 3;

Reference yield:

Clomipramine (303-49-1,83162-38-3) → clomipramine hydrochloride (17321-77-6)

Guidance literature:

With hydrogenchloride; In toluene;

upstream raw materials:

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine

3-dimethylaminopropionic acid

3-(Dimethylamino)propyl chloride

Clomipramine

Downstream raw materials:

3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepine

Refernces

• 1、 -. "High-purity clomipamine hydrochloride and preparation method thereof". Paragraph 0084-0086; 0089; 0097-0106; 0112-0118; 0124-0129. . Retrieved 2020/11/23.