Manidipine

Manidipine is a calcium channel blocker (dihydropyridine type) that is used clinically as an antihypertensive.^{[1][2][3][4][5]}

Manidipine

Clinical data
Trade names	Manyper, Caldine, etc.
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	C08CA11 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (±)-2-[4-(Diphenylmethyl)piperazin-1-yl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number	89226-50-6 120092-68-4
PubChem CID	4008
ChemSpider	3868
UNII	6O4754US88
CompTox Dashboard (EPA)	DTXSID2043745
Chemical and physical data
Formula	C35H38N4O6
Molar mass	610.711 g·mol−1
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c1cccc(c1)C5C(/C(=O)OC)=C(\N\C(=C5\C(=O)OCCN4CCN(C(c2ccccc2)c3ccccc3)CC4)C)C
InChI InChI=1S/C35H38N4O6/c1-24-30(34(40)44-3)32(28-15-10-16-29(23-28)39(42)43)31(25(2)36-24)35(41)45-22-21-37-17-19-38(20-18-37)33(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-16,23,32-33,36H,17-22H2,1-3H3

It was patented in 1982 and approved for medical use in 1990.^[6]

Synthesis

Thieme Synthesis:^[7] Patent:^[8] Sino:^{[9][10][11][12][13][14][15]}

The alkylation between N-(2-hydroxyethyl)piperazine [103-76-4] (1) and Benzhydryl Bromide [776-74-9] (2) gives 2-(4-benzhydrylpiperazin-1-yl)ethanol [10527-64-7] (3). The reaction with Diketene [674-82-8] (4) gives 2-(4-benzhydryl-1-piperazinyl)ethyl acetoacetate [89226-49-3] (5). The reaction with 3-nitrobenzaldehyde [99-61-6] (6) and Methyl 3-aminocrotonate [14205-39-1] (7) completed the synthesis of Manidipine (8).