Doxepinol

Base Information

• Chemical Name: Doxepinol
• CAS No.: 4504-88-5
• Molecular Formula: C19H23 N O2
• Molecular Weight: 297.397
• Hs Code.: 2932996560
• European Community (EC) Number: 224-821-0
• UNII: 7O29I2R0ZG
• DSSTox Substance ID: DTXSID70963330
• Nikkaji Number: J42.218E
• Wikidata: Q27268630
• Mol file: 4504-88-5.mol

Synonyms:Doxepinol;4504-88-5;Doxepin EP Impurity B;11-[3-(dimethylamino)propyl]-6H-benzo[c][1]benzoxepin-11-ol;EINECS 224-821-0;BRN 1292658;UNII-7O29I2R0ZG;7O29I2R0ZG;11-(3-(dimethylamino)propyl)-6,11-dihydrodibenzo[b,e]oxepin-11-ol;11-Hydroxy-11-(3-dimethylaminopropyl)-6,11-dihydrodibenz(b,e)oxepine;Dibenz(b,e)oxepin-11-propylamine, 6,11-dihydro-N,N-dimethyl-11-hydroxy-;DIBENZ(b,e)OXEPIN-11-OL, 6,11-DIHYDRO-11-(3-DIMETHYLAMINOPROPYL)-;11-(3-(Dimethylamino)propyl)-6,11-dihydrodibenz(b,e)oxepin-11-ol;11-[3-(dimethylamino)propyl]-6,11-dihydrodibenz[b,e]oxepin-11-ol;11-[3-(Dimethylamino)propyl]-6,11-dihydrodibenzo[b,E]oxepin-11-ol;Dibenz(b,e)oxepin-11-ol, 11-(3-(dimethylamino)propyl)-6,11-dihydro-;Dibenz[b,e]oxepin-11-ol, 11-[3-(dimethylamino)propyl]-6,11-dihydro-;(11RS)-11-[3-(Dimethylamino)-propyl]-6,11-dihydrodibenzo[b,e]oxepin-11-ol (Doxepinol);11-(3-(dimethylamino)propyl)-6,11-dihydrodibenz[b,e]oxepin-11-ol;DOXEPIN IMPURITY B;(+/-)-DOXEPINOL;SCHEMBL1281911;DTXSID70963330;LS-61636;CS-0179842;DOXEPIN HYDROCHLORIDE IMPURITY B [EP IMPURITY];Q27268630;11-(3-Dimethylaminopropyl)-6,11-dihydrobenz[b,e]oxepin-11-hydroxy;11-[3-(Dimethylamino)propyl]-6,11-dihydrocibenz[b,e]oxepin-11-ol;11-[3-(Dimethylamino)propyl]-6,11-dihydrodibenzo[b,E]oxepin-11-ol #;11(RS)-(3-(DIMETHYLAMINO)PROPYL)-6,11-DIHYDRODIBENZO(B,E)OXEPIN-11-OL;11-[3-(diMethylaMino)propyl]-6,11-dihydrodibenz[b,e]oxepin-11-ol (Doxepin Impurity);2-[3-(dimethylamino)propyl]-9-oxatricyclo[9.4.0.0?,?]pentadeca-1(11),3,5,7,12,14-hexaen-2-ol

Chemical Property of Doxepinol

Chemical Property:

• Vapor Pressure: 1.73E-08mmHg at 25°C
• Boiling Point: 439.2°Cat760mmHg
• Flash Point: 219.4°C
• PSA: 32.70000
• Density: 1.123g/cm³
• LogP: 3.15670
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 297.172878976
• Heavy Atom Count: 22
• Complexity: 359

Purity/Quality:

99.9% ^*data from raw suppliers

11-[3-(Dimethylamino)propyl]-6,11-dihydrocibenz[b,e]oxepin-11-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCCC1(C2=CC=CC=C2COC3=CC=CC=C31)O
• Uses: 11-[3-(Dimethylamino)propyl]-6,11-dihydrocibenz[b,e]oxepin-11-ol is an impurity in the synthesis of Doxepin (D550000), used clinically to treat anxiety and depression. Doxepin is an antidepressant.

Technology Process of Doxepinol

There total 3 articles about Doxepinol 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:

6,11-dihydrodibenz[b,e]oxepin-11-one (4504-87-4) + 3-Dimethylaminopropylmagnesium-chlorid → 11-[3-(dimethylamino)propyl]-6,11-dihydrodibenz[b,e]oxepin-11-ol (4504-88-5)

Guidance literature:

In toluene; at 40 ℃; for 1h; Temperature;

Reference yield:

3-(Dimethylamino)propyl chloride (109-54-6) → 11-[3-(dimethylamino)propyl]-6,11-dihydrodibenz[b,e]oxepin-11-ol (4504-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: methyl iodide; magnesium; iodine / toluene; tetrahydrofuran / 2 h / 55 °C

2: toluene / 1 h / 40 °C

With iodine; magnesium; methyl iodide; In tetrahydrofuran; toluene;

Reference yield:

→ 11-[3-(dimethylamino)propyl]-6,11-dihydrodibenz[b,e]oxepin-11-ol (4504-88-5)

Guidance literature:

11-Oxo-6,11-dihydro-dibenzooxepin, 3-Dimethylamino-propylmagnesiumchlorid (THF, 16h, Siedetemp.);

DOI:10.1021/jm01241a012

upstream raw materials:

3-(Dimethylamino)propyl chloride

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

Downstream raw materials:

doxepin

Refernces