E-10-Hydroxynortriptyline

Base Information

• Chemical Name: E-10-Hydroxynortriptyline
• CAS No.: 47132-16-1
• Molecular Formula: C19H21NO
• Molecular Weight: 279.3761
• UNII: OT3006Y33U,K2M3MUO01G,CD85QI7QOV
• Nikkaji Number: J566.423C,J346.735J
• Metabolomics Workbench ID: 42515
• ChEMBL ID: CHEMBL5174395
• Mol file: 47132-16-1.mol

Synonyms:E-10-Hydroxynortriptyline;47132-16-1;(E)-10-Hydroxynortriptyline;trans-10-Hydroxynortriptyline;10-Hydroxy-(E)-nortriptyline;UNII-CD85QI7QOV;CD85QI7QOV;K2M3MUO01G;UNII-OT3006Y33U;10-Hydroxynortriptyline, (E)-;(+)-E-10-OH-Nt;OT3006Y33U;5H-Dibenzo(a,d)cyclohepten-10-ol, 10,11-dihydro-5-(3-(methylamino)propylidene)-, (E)-;(E)-10-Hydroxy Nortriptyline maleate;10-Hydroxynortriptyline, (E)-(+)-;10-Hydroxynortriptyline, (E)-(-)-;112839-35-7;trans-10-hydroxy Nortriptyline;(E)-10,11-Dihydro-5-(3-(methylamino)propylidene)-5H-dibenzo(a,d)cyclohepten-10-ol;5H-Dibenzo(a,d)cyclohepten-10-ol, 10,11-Dihydro-5-(3-(methylamino)propylidene)-;(2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol;112839-36-8;5H-Dibenzo(a,d)cyclohepten-10-ol, 10,11-dihydro-5-(3-(methylamino)propylidene)-, (5E)-(+)-;()-TRANS-10-HYDROXYNORTRIPTYLINE;(E)-10-Hydroxy Nortriptyline;5H-Dibenzo[a,d]cyclohepten-10-ol, 10,11-dihydro-5-[3-(methylamino)propylidene]-;E-10-OH-nortriptyline;UNII-K2M3MUO01G;SCHEMBL2739084;CHEMBL5174395;(-)-E-10-OH-NT;HY-U00050;AKOS040756245;SMP2_000114;MS-23967;CS-0021940;10-HYDROXYNORTRIPTYLINE, (E)-(+/-)-;(E)-5-(3-(Methylamino)propylidene)-10,11-dihydro-5H-dibenzo[a,d][7]annulen-10-ol;(2E)-2-[3-(methylamino)propylidene]tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-ol;(5E)-10,11-DIHYDRO-5-(3-(METHYLAMINO)PROPYLIDENE)-5H-DIBENZO(A,D)CYCLOHEPTEN-10-OL;5H-DIBENZO(A,D)CYCLOHEPTEN-10-OL, 10,11-DIHYDRO-5-(3-(METHYLAMINO)PROPYLIDENE)-, (5E)-;5H-DIBENZO(A,D)CYCLOHEPTEN-10-OL, 10,11-DIHYDRO-5-(3-(METHYLAMINO)PROPYLIDENE)-, (5E)-(-)-;5H-Dibenzo(a,d)cyclohepten-10-ol, 10,11-dihydro-5-(3-(methylamino)propylidene)-, (E)-(-)-

Chemical Property of E-10-Hydroxynortriptyline

Chemical Property:

• Vapor Pressure: 2.42E-09mmHg at 25°C
• Boiling Point: 462.3°Cat760mmHg
• Flash Point: 142.1°C
• PSA: 32.26000
• Density: 1.164g/cm³
• LogP: 3.70820
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 279.162314293
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

99%min ^*data from raw suppliers

(E)-10-Hydroxynortriptyline 99.66% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCC=C1C2=CC=CC=C2CC(C3=CC=CC=C31)O
• Isomeric SMILES: CNCC/C=C/1\C2=CC=CC=C2CC(C3=CC=CC=C31)O
• Uses: 10-Hydroxy-(E)-nortriptyline is an intermediate in the synthesis of 10-Hydroxy Nortriptyline Maleate (H948820), a metabolite of Nortriptyline (N837000).

Technology Process of E-10-Hydroxynortriptyline

There total 12 articles about E-10-Hydroxynortriptyline 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: 89.0%

(+)-E-5-(γ-bromopropylidene)-10,11-dihydro-10-hydroxy-5H-dibenzo[a,d]-cycloheptene (156458-95-6) + methylamine (74-89-5) → (E)-10-Hydroxynortriptyline (47132-16-1,112839-35-7,112839-36-8)

Guidance literature:

In acetonitrile; at 60 ℃; for 5h;

DOI:10.1080/00397919408010157

Reference yield:

10-piperidin-1-yl-dibenzo[a,d]cyclohepten-5-one (37439-92-2) → (E)-10-Hydroxynortriptyline (47132-16-1,112839-35-7,112839-36-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 3 h / 0 °C

2: 48percent HBr / acetic acid / Heating

3: 100 percent / NaBH₄ / methanol / 1 h / Ambient temperature

4: 89 percent / acetonitrile / 5 h / 60 °C

With sodium tetrahydroborate; hydrogen bromide; In tetrahydrofuran; methanol; acetic acid; acetonitrile;

DOI:10.1080/00397919408010157

Reference yield:

5-cyclopropyl-10-piperidin-1-yl-5H-dibenzo[a,d]cyclohepten-5-ol (156458-93-4) → (E)-10-Hydroxynortriptyline (47132-16-1,112839-35-7,112839-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 48percent HBr / acetic acid / Heating

2: 100 percent / NaBH₄ / methanol / 1 h / Ambient temperature

3: 89 percent / acetonitrile / 5 h / 60 °C

With sodium tetrahydroborate; hydrogen bromide; In methanol; acetic acid; acetonitrile;

DOI:10.1080/00397919408010157

upstream raw materials:

(E)-N-methyl-3-(10,11-dihydro-10-oxo-5H-dibenzocycloheptene)-Δ^5,γ-propylamine

(+)-E-5-(γ-bromopropylidene)-10,11-dihydro-10-hydroxy-5H-dibenzo[a,d]-cycloheptene

methylamine

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Refernces

• 1、 Jean-Claude,Just. "Facile synthesis of (R,S)-(Z) and (R,S)-(E)-N-methyl-(10,11-dihydro-10- hydroxy-5H-dibenzo[a,d]cycloheptene)-Δ(5,γ)-propylamine the major metabolites of amitriptyline and nortriptyline". . p. 1565 - 1573. Retrieved 2007/10/02.