Dilevalol hydrochloride

Base Information

• Chemical Name: Dilevalol hydrochloride
• CAS No.: 75659-08-4
• Molecular Formula: C19H24 N2 O3 . Cl H
• Molecular Weight: 364.87
• UNII: O5OBT75D2C
• DSSTox Substance ID: DTXSID7020477
• Wikidata: Q27285375
• NCI Thesaurus Code: C174786
• ChEMBL ID: CHEMBL1204165
• Mol file: 75659-08-4.mol

Synonyms:AH 5158;AH-5158;AH5158;Albetol;Apo Labetalol;Apo-Labetalol;ApoLabetalol;Dilevalol;Hydrochloride, Labetalol;Labetalol;Labetalol Hydrochloride;Labetalol, (R,R)-Isomer;Labetolol;Normodyne;Presolol;R,R Labetalol;R,R-Labetalol;SCH 19927;SCH-19927;SCH19927;Trandate

Chemical Property of Dilevalol hydrochloride

Chemical Property:

• Vapor Pressure: 4.75E-13mmHg at 25°C
• Melting Point: 192-193.5 °C (decomp)
• Boiling Point: 552.7°C at 760 mmHg
• Flash Point: 288.1°C
• PSA: 95.58000
• LogP: 4.02860
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 364.1553704
• Heavy Atom Count: 25
• Complexity: 385

Purity/Quality:

98%Min ^*data from raw suppliers

(R,R)-LabetalolHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCC1=CC=CC=C1)NCC(C2=CC(=C(C=C2)O)C(=O)N)O.Cl
• Isomeric SMILES: C[C@H](CCC1=CC=CC=C1)NC[C@@H](C2=CC(=C(C=C2)O)C(=O)N)O.Cl
• Uses: Antihypertensive:anti-adrenergic (β-receptor). (R,R)-Labetalol Hydrochloride is a specific competitive antagonist at both α-and β-adrenergic receptor sites. (R,R)-Labetalol Hydrochloride is also used as an antihypertensive.

Technology Process of Dilevalol hydrochloride

There total 5 articles about Dilevalol hydrochloride 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:

5-<(R)-1-hydroxy-2-<<(R)-1-methyl-3-phenylpropyl>(phenylmethyl)amino>ethyl>-2-(phenylmethoxy)benzamide hydrochloride (75615-54-2) → (R,R)-Labetalol hydrochloride (75659-08-4) + (+)-(R)-2-hydroxy-5-<2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide hydrochloride (83167-30-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 2h; under 2280 Torr; Ambient temperature;

DOI:10.1021/jm00353a017

Reference yield:

(R)-2-hydroxy-5-[[N-(1-methyl-3-phenylpropyl)-N-(phenylmethyl)amino]acetyl] benzamide hydrochloride → *)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide hydrochloride (81602-13-3) + (R,R)-Labetalol hydrochloride (75659-08-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 4h; under 760.051 Torr; Overall yield = 100 %;

DOI:10.1016/j.mcat.2018.02.017

Reference yield:

(RS)-1-methyl-3-phenylpropylamine (22374-89-6,22148-77-2,1199266-89-1) → *)>-2-hydroxy-5-<1-hydroxy-2-<(1-methyl-3-phenylpropyl)amino>ethyl>benzamide hydrochloride (81602-13-3) + (R,R)-Labetalol hydrochloride (75659-08-4)

Guidance literature:

Multi-step reaction with 4 steps

1: Novozym 435 / toluene / 120 h / 45 °C / Molecular sieve; Resolution of racemate

2: lithium aluminium tetrahydride / 20 °C

3: butanone / 1 h / Reflux

4: palladium 10% on activated carbon; hydrogen / ethanol / 4 h / 20 °C / 760.05 Torr

With lithium aluminium tetrahydride; palladium 10% on activated carbon; hydrogen; butanone; In ethanol; toluene;

DOI:10.1016/j.mcat.2018.02.017

upstream raw materials:

5-<(R)-1-hydroxy-2-<<(R)-1-methyl-3-phenylpropyl>(phenylmethyl)amino>ethyl>-2-(phenylmethoxy)benzamide hydrochloride

5-(2-bromoacetyl)-2-hydroxybenzamide

(+)-(R)-α-methyl-N-(phenylmethyl)benzenepropanamine

(RS)-1-methyl-3-phenylpropylamine

Downstream raw materials:

2-Hydroxy-5-[1-hydroxy-2-((R)-1-methyl-3-phenyl-propylamino)-ethyl]-benzamide

(S,R)-labetalol

C₁₉H₂₃NO₄

Refernces

• 1、 Gold, Elijah H.,Chang, Wei,Cohen, Marvin,Baum, Thomas,Ehrreich, Steward,et al.. "Synthesis and Comparison of Some Cardiovascular Properties of the Stereoisomers of Labetalol". . p. 1363 - 1370. Retrieved 2007/10/02.