Hydrochloric Acid → HCID 19871216, compound

HRID 329855Notes

Reaction equation

HRID 329855 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)(=[O:17])[CH2:13][C:14]([CH3:16])=O.[NH2:34]/[C:35](/[CH3:41])=[CH:36]\[C:37]([O:39][CH3:40])=[O:38].[ClH:42]>C(O)(C)C.O1CCOCC1>[ClH:42].[CH3:16][C:14]1[NH:34][C:35]([CH3:41])=[C:36]([C:37]([O:39][CH3:40])=[O:38])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:13]=1[C:12]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 153212052-[4-(4-Fluorophenyl)piperazin-1-yl]ethyl 3-oxobutanoate

Product 1

HCID 19871216HCID 19871216, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of m-nitrobenzaldehyde, 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl acetoacetate and methyl 3-aminocrotonate was worked up in isopropyl alcohol in the same manner as Example 1, and the product obtained was further treated with a dioxane solution of hydrogen chloride to give 2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride as a light yellow powder, m.p. 108°-110° C. Yield 76.4%. NMR(DMSO-d6) δ: 2.30(3H,s, ##STR27## 2.38(3H,s, ##STR28## 3.60(3H,s,COOCH3), 4.48(2H,m,--COOCH2CH2 --), 5.03(1H,s,C(4) --H).

Workup

  1. customthe product obtained

Sources & evidence

ORD record
ord-517c9c306a0e447da53b907030f40733
Source dataset
uspto-grants-1990_01
Patent number
US04892875

Reaction notes

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