(E)-Desmethyldoxepin

Base Information

• Chemical Name: (E)-Desmethyldoxepin
• CAS No.: 1225-56-5
• Molecular Formula: C₁₈H₁₉NO
• Molecular Weight: 265.355
• Hs Code.: 2932999099
• UNII: J7JTC0A5D6
• DSSTox Substance ID: DTXSID60217319
• Nikkaji Number: J1.251.189B,J268.169B
• Wikipedia: Nordoxepin
• Wikidata: Q27281308
• Mol file: 1225-56-5.mol

Synonyms:demethyldoxepin;desmethyldoxepin;desmethyldoxepin hydrochloride;desmethyldoxepin, (E)-isomer;desmethyldoxepin, (Z)-isomer;nordoxepin

Chemical Property of (E)-Desmethyldoxepin

Chemical Property:

• Vapor Pressure: 2.74E-07mmHg at 25°C
• Melting Point: 63-65℃
• Refractive Index: 1.5100 (estimate)
• Boiling Point: 420.8°Cat760mmHg
• PKA: pKa 9.75(I=0.00 t=25.0) (Uncertain)
• Flash Point: 174.5°C
• PSA: 21.26000
• Density: 1.134g/cm³
• LogP: 4.01110
• Storage Temp.: ?20°C
• Water Solubility.: 104.8mg/L(25 oC)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 265.146664230
• Heavy Atom Count: 20
• Complexity: 338

Purity/Quality:

98%,99%, ^*data from raw suppliers

Desmethyldoxepin solution cis/trans, 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCC=C1C2=CC=CC=C2COC3=CC=CC=C31
• Isomeric SMILES: CNCC/C=C/1\C2=CC=CC=C2COC3=CC=CC=C31
• Uses: Desmethyldoxepin solution may be used as an internal standard in the high performance liquid chromatographic (HPLC) determination of bupivacaine in samples of human serum.

Technology Process of (E)-Desmethyldoxepin

There total 5 articles about (E)-Desmethyldoxepin 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: 50.0%

11-<3-(N-Methyl-N-ethoxycarbonylamino)-propyliden>-6,11-dihydro-dibenzooxepin (2895-62-7) → Desmethyldoxepin (1225-56-5)

Guidance literature:

With potassium hydroxide; In butan-1-ol; for 4h; Heating;

DOI:10.1248/cpb.41.1987

Reference yield:

C21H20Cl3NO3 → Desmethyldoxepin (1225-56-5)

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran; at 30 - 50 ℃; for 2.5h; Temperature; Solvent;

Reference yield:

6,11-dihydrodibenz[b,e]oxepin-11-one (4504-87-4) + [3-(methylamino)propyl](triphenyl)phosphonium bromide hydrobromide (4174-83-8) → Desmethyldoxepin (1225-56-5)

Guidance literature:

[3-(methylamino)propyl](triphenyl)phosphonium bromide hydrobromide; With n-butyllithium; In tetrahydrofuran; n-heptane; for 1.5h;

6,11-dihydrodibenz[b,e]oxepin-11-one; In tetrahydrofuran; n-heptane; for 10h; Heating / reflux;

With hydrogenchloride; In water; pH=2;

upstream raw materials:

11-<3-(N-Methyl-N-ethoxycarbonylamino)-propyliden>-6,11-dihydro-dibenzooxepin

doxepin hydrochloride

6,11-dihydrodibenz[b,e]oxepin-11-one

[3-(methylamino)propyl](triphenyl)phosphonium bromide hydrobromide

Downstream raw materials:

3-(6H-dibenzoxepin-11-ylidene)-N-methylpropylamine hydrochloride

Refernces

• 1、 -. "Synthetic method of demethylated doxepin hydrochloride". . . Retrieved 2021/01/25.
• 2、 Muramatsu,Sawanishi,Iwasaki,Kakiuchi,Ohashi,Kato,Ito. "Study on zwitter-ionization of drugs. II. Synthesis and pharmacological activity of some N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N- methylamino- and N-[3-(6H-dibenz[b,e]oxepin-11-ylidene)propyl]-N-methylamino- alkanoic acid derivatives and related compounds". . p. 1987 - 1993. Retrieved 2007/10/02.