BENIDIPINE HYDROCHLORIDE

Base Information

• Chemical Name: BENIDIPINE HYDROCHLORIDE
• CAS No.: 91599-76-7
• Molecular Formula: C₂₈H₃₁N₃O₆*ClH
• Molecular Weight: 542.032
• Mol file: 91599-76-7.mol

Synonyms:3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (R*,S*)-(±)-;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 1-(phenylmethyl)-3-piperidinyl ester, monohydrochloride, (R*,S*)-;Benidipine hydrochloride;

Chemical Property of BENIDIPINE HYDROCHLORIDE

Chemical Property:

• PSA: 113.69000
• LogP: 5.80230

Purity/Quality:

97% ^*data from raw suppliers

(R,S)(S,R)-BenidipineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R,S)(S,R)-Benidipine Hydrochloride is an impurity of the drug Benidipine (B157500).

Technology Process of BENIDIPINE HYDROCHLORIDE

There total 17 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: 70.5%

1-benzyl-3-hydroxypiperidine (14813-01-5) + 5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid (74936-72-4) → KW 3049 (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; In dichloromethane; N,N-dimethyl-formamide; for 1h; Cooling with ice;

1-benzyl-3-hydroxypiperidine; In dichloromethane; N,N-dimethyl-formamide; at 20 - 30 ℃; for 1h;

With hydrogenchloride; In water; at 20 ℃; for 1h; Reagent/catalyst;

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;

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

methyl 2-(3-nitrophenylmethylene)acetoacetate

Refernces

• 1、 -. "A benidipine hydrochloride method for synthesizing intermediate". Paragraph 0009; 0048-0050. . Retrieved 2018/07/30.
• 2、 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.