2-Hydroxydesipramine

Base Information

• Chemical Name: 2-Hydroxydesipramine
• CAS No.: 1977-15-7
• Deprecated CAS: 112663-90-8
• Molecular Formula: C18H22 N2 O
• Molecular Weight: 282.38
• Hs Code.: 2933990090
• UNII: VO1Y07E90C
• DSSTox Substance ID: DTXSID20173467
• Nikkaji Number: J72.774A
• Wikidata: Q27216291
• Mol file: 1977-15-7.mol

Synonyms:2-hydroxy-desipramine;2-hydroxydesipramine;2-hydroxydesipramine fumarate;2-hydroxydesipramine monofumarate;2-hydroxydesipramine monohydrochloride;2-hydroxydesmethylimipramine;2-OH-DMI

Chemical Property of 2-Hydroxydesipramine

Chemical Property:

• Vapor Pressure: 9.32E-10mmHg at 25°C
• Melting Point: 146-148°C
• Boiling Point: 477.9°Cat760mmHg
• Flash Point: 242.8°C
• PSA: 35.50000
• Density: 1.117g/cm³
• LogP: 3.69430
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly), Dichloromethane (Very Slightly, Heated), Methanol (Slightly）
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 282.173213330
• Heavy Atom Count: 21
• Complexity: 322

Purity/Quality:

98%Min ^*data from raw suppliers

2-Hydroxy Desipramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCCN1C2=C(CCC3=CC=CC=C31)C=C(C=C2)O
• Uses: A metabolite of Desipramine A metabolite of Desipramine.

Technology Process of 2-Hydroxydesipramine

There total 6 articles about 2-Hydroxydesipramine 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: 99.0%

N-Benzyl-2-hydroxydesipramine (134150-71-3) → 2-Hydroxydesipramine (1977-15-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 5h; under 760 Torr;

Reference yield:

N-Benzyldesipramine (3978-87-8) → 2-Hydroxydesipramine (1977-15-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / POCl₃ / 4 h / 100 °C

2: m-CPBA; TFA / CH₂Cl₂ / 2 h / 5 - 20 °C

3: conc. HCl / methanol / 2 h

4: 99 percent / H₂ / 10 percent Pd/C / ethanol / 5 h / 760 Torr

With hydrogenchloride; hydrogen; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trichlorophosphate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; 1: Formylation / 2: Oxidation / 3: Hydrolysis / 4: Catalytic hydrogenation;

Reference yield:

desipramine hydrochloride (58-28-6) → 2-Hydroxydesipramine (1977-15-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 48 percent / KOH; NaBH₃CN / methanol

2: 68 percent / POCl₃ / 4 h / 100 °C

3: m-CPBA; TFA / CH₂Cl₂ / 2 h / 5 - 20 °C

4: conc. HCl / methanol / 2 h

5: 99 percent / H₂ / 10 percent Pd/C / ethanol / 5 h / 760 Torr

With hydrogenchloride; potassium hydroxide; hydrogen; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; trichlorophosphate; palladium on activated charcoal; In methanol; ethanol; dichloromethane; 1: reductive amination; N-benzylation / 2: Formylation / 3: Oxidation / 4: Hydrolysis / 5: Catalytic hydrogenation;

upstream raw materials:

N-Benzyl-2-hydroxydesipramine

N-Benzyldesipramine

desipramine hydrochloride

N-Benzyl-2-formyldesipramine

Refernces

• 1、 Adamczyk, Maciek,Chen, Yon-Yih,Fishpaugh, Jeffrey R.. "A FACILE SYNTHETIC ROUTE TO HYDROXY METABOLITES OF TRICYCLIC ANTIDEPRESSANTS". . p. 365 - 372. Retrieved 2007/10/03.