Naftopidil, (S)-

Base Information

• Chemical Name: Naftopidil, (S)-
• CAS No.: 127931-16-2
• Molecular Formula: C24H28 N2 O3
• Molecular Weight: 392.498
• UNII: F4FVQ50FFI
• Nikkaji Number: J277.915C
• Wikidata: Q27277626
• Mol file: 127931-16-2.mol

Synonyms:Naftopidil, (S)-;(+)-Naftopidil;S-(+)-Naftopidil;Naftopidil, (+)-;UNII-F4FVQ50FFI;F4FVQ50FFI;127931-16-2;S-(-)-Naftopidil;1-Piperazineethanol, 4-(2-methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-, (alphaS)-;1-Piperazineethanol, 4-(2-methoxyphenyl)-alpha-((1-naphthalenyloxy)methyl)-, (S)-;(2S)-1-[4-(2-methoxyphenyl)piperazin-1-yl]-3-naphthalen-1-yloxypropan-2-ol;(S)-naftopidil;SCHEMBL8819142;Q27277626;1-PIPERAZINEETHANOL, 4-(2-METHOXYPHENYL)-.ALPHA.-((1-NAPHTHALENYLOXY)METHYL)-, (.ALPHA.S)-;1-PIPERAZINEETHANOL, 4-(2-METHOXYPHENYL)-.ALPHA.-((1-NAPHTHALENYLOXY)METHYL)-, (S)-

Chemical Property of Naftopidil, (S)-

Chemical Property:

• PSA: 45.17000
• LogP: 3.41320
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 392.20999276
• Heavy Atom Count: 29
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1N2CCN(CC2)CC(COC3=CC=CC4=CC=CC=C43)O
• Isomeric SMILES: COC1=CC=CC=C1N2CCN(CC2)C[C@@H](COC3=CC=CC4=CC=CC=C43)O

Technology Process of Naftopidil, (S)-

There total 12 articles about Naftopidil, (S)- 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: 93.0%

1-(2-Methoxyphenyl)piperazine (35386-24-4) + (S)-(1-naphthyl) glycidyl ether (61249-00-1) → (S)-(-)-1-<4-(2-Methoxyphenyl)-1-piperazinyl>-3-(1-naphthyloxy)-2-propanol (127931-16-2)

Guidance literature:

In isopropyl alcohol; for 30h; Heating;

DOI:10.1246/cl.2004.1212 DOI:10.1055/s-2005-870021

Reference yield: 48.0%

α-naphthol (90-15-3) + (S)-1-(2-methoxy-phenyl)-4-oxiranylmethyl-piperazine (1621070-08-3) → (S)-(-)-1-<4-(2-Methoxyphenyl)-1-piperazinyl>-3-(1-naphthyloxy)-2-propanol (127931-16-2)

Guidance literature:

With tetrabutyl ammonium fluoride; silver nitrate; In isopropyl alcohol; at 60 - 80 ℃; for 13h; regioselective reaction;

DOI:10.1016/j.molcata.2014.05.011

Reference yield:

2-methoxy-phenylamine (90-04-0) → (S)-(-)-1-<4-(2-Methoxyphenyl)-1-piperazinyl>-3-(1-naphthyloxy)-2-propanol (127931-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / aq. Na₂CO₃; benzyltriethyl ammonium chloride / 24 h / 100 °C

2.1: K₂CO₃ / acetonitrile / Heating

2.2: zinc(II) perchlorate hexahydrate / 0.17 h / 80 °C

With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate; potassium carbonate; In acetonitrile;

DOI:10.1021/jo062674j

upstream raw materials:

1-(2-Methoxyphenyl)piperazine

(S)-(1-naphthyl) glycidyl ether

(S)-epichlorohydrin

α-naphthol

Refernces

• 1、 Seth, Kapileswar,Roy, Sudipta Raha,Kommi, Damodara N.,Pipaliya, Bhavin V.,Chakraborti, Asit K.. "Silver nanoparticle-catalysed phenolysis of epoxides under neutral conditions: Scope and limitations of metal nanoparticles and applications towards drug synthesis". . p. 164 - 172. Retrieved 2014/06/23.
• 2、 Lokhande, Mahendra N.,Chopade, Manojkumar U.,Bhangare, Dattatrya N.,Nikalje, Milind D.. "Asymmetric synthesis of propranolol, naftopidil and (R)-monobutyrin using a glycerol desymmetrization strategy". . p. 406 - 409. Retrieved 2013/08/25.