Dicyclohexylcarbodiimide → Manidipine

HRID 1475169Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:9]([C:20]([OH:22])=[O:21])=[C:8]([CH3:23])[NH:7][C:6]=1[CH3:24])=[O:4].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[CH:49]([N:62]1[CH2:67][CH2:66][N:65]([CH2:68][CH2:69]O)[CH2:64][CH2:63]1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1(C)C=CC=CC=1>[CH3:24][C:6]1[NH:7][C:8]([CH3:23])=[C:9]([C:20]([O:22][CH2:69][CH2:68][N:65]2[CH2:64][CH2:63][N:62]([CH:49]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=3)[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:67][CH2:66]2)=[O:21])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

Conditions

Temperature: 72.5 °C

Procedure

To a suspension of 2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid monomethyl ester (5 gm), dicyclohexyl carbodiimide (3.08 gm) and dimethylamino pyridine (0.25 gm) in toluene (30 ml) at room temperature was added 2-(4-benzhydryl piperazine-1-yl)ethanol (7.5 gm). Reaction mass was then heated to 70-75° C. for 2 hours. Reaction mass was then cooled to room temperature and filtered. Toluene layer was concentrated under vacuum to get manidipine base (5 gm).

Workup

customReaction mass
customReaction mass
temperaturewas then cooled to room temperature
filtrationfiltered
concentrationToluene layer was concentrated under vacuum

Sources & evidence

ORD record: ord-560eb7a71ae64a37af1fd5388192132e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018376B2

Reaction notes

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