Benidipine hydrochloride

Base Information

• Chemical Name: Benidipine hydrochloride
• CAS No.: 91599-74-5
• Deprecated CAS: 105993-05-3
• Molecular Formula: C28H32ClN3O6
• Molecular Weight: 542.032
• Hs Code.: 2942000000
• European Community (EC) Number: 663-500-3
• UNII: 0A6746FWDL
• DSSTox Substance ID: DTXSID2049050
• Wikidata: Q27236529
• NCI Thesaurus Code: C81677
• ChEMBL ID: CHEMBL2359165,CHEMBL3190257
• Mol file: 91599-74-5.mol

Synonyms:1,4 dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester HCl;benidipine hydrochloride;KW 3049;KW-3049

Chemical Property of Benidipine hydrochloride

Chemical Property:

• Melting Point: 199-201oC
• Boiling Point: 625.2 °C at 760 mmHg
• PKA: 7.34(at 25℃)
• Flash Point: 331.9 °C
• PSA: 124.28000
• LogP: 3.74270
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: ≥20mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 541.1979634
• Heavy Atom Count: 38
• Complexity: 933

Purity/Quality:

99% ^*data from raw suppliers

racBenidipineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC2CCCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC.Cl
• Isomeric SMILES: CC1=C([C@H](C(=C(N1)C)C(=O)O[C@@H]2CCCN(C2)CC3=CC=CC=C3)C4=CC(=CC=C4)[N+](=O)[O-])C(=O)OC.Cl
• Description: Benidipine hydrochloride is a new, long acting dihydropyridine calcium antagonist useful in the treatment of hypertension and angina pectoris. In experimental animals, benidipine hydrochloride dose dependently induced hypotension with a potency of 6 and 12 times more than nifedipine and nicardipine, respectively. It also exhibited a slow onset of action. Benidipine is an orally bioavailable blocker of L-, T-, and N-type calcium channels. In guinea pig ventricular cells benidipine has an IC50 of 2.7 nM for calcium currents, determined using whole cell voltage clamp electrophysiology. It prevents oxidative stress dose-dependently in vitro, decreases blood pressure in spontaneously hypertensive rats (at 3 and 10 mg/kg), and is neuroprotective for neural stem cells after oxidative stress-induced injury. Benidipine is also a competitive antagonist at mineralocorticoid receptors.

Technology Process of Benidipine hydrochloride

There total 3 articles about Benidipine 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: 36.2%

1-benzyl-3-hydroxypiperidine (14813-01-5) + 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4) → benidipine hydrochloride (91599-74-5,129262-07-3,85387-35-5,91599-76-7)

Guidance literature:

5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid; With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Sonographic reaction; Cooling with ice;

1-benzyl-3-hydroxypiperidine; In dichloromethane; for 2.5h; Cooling with ice; Sonographic reaction;

Reference yield:

5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4) → benidipine hydrochloride (91599-74-5,129262-07-3,85387-35-5,91599-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / dimethylformamide; CH₂Cl₂ / 1 h

2: dimethylformamide; CH₂Cl₂ / 2.5 h

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

1-benzyl-3-hydroxypiperidine (14813-01-5) + 1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride (88712-56-5,125185-92-4) → benidipine hydrochloride (91599-74-5,129262-07-3,85387-35-5,91599-76-7) + (RS)-(SR)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester hydrochloride (129262-07-3,85387-35-5,91599-76-7)

Guidance literature:

In dichloromethane; N,N-dimethyl-formamide; for 2.5h; Yield given. Yields of byproduct given;

upstream raw materials:

1-benzyl-3-hydroxypiperidine

1,4-dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-5-carboxylic acid chloride

5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid

Refernces

• 1、 Muto,Kuroda,Kawato,Karasawa,Kubo,Nakamizo. "Synthesis and pharmacological activity of stereoisomers of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl 1-(phenylmethyl)-3-piperidinyl ester". . p. 1662 - 1665. Retrieved 2007/10/02.