Hydrochloric Acid → HCID 17766916, compound

HRID 2107958Notes

Reaction equation

HRID 2107958 reaction equation
Cl.Cl.[CH3:3][C:4]1[NH:5][C:6]([CH3:37])=[C:7]([C:33]([O:35][CH3:36])=[O:34])[CH:8]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=2)[C:9]=1[C:10]([O:12][CH2:13][C:14]([CH3:23])([CH3:22])[CH2:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:11].C(N(CC)CC)C.[O:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[C:50]([Cl:52])=[O:51].Cl>O1CCCC1.C(OCC)C.C(O)C>[ClH:52].[CH3:3][C:4]1[NH:5][C:6]([CH3:37])=[C:7]([C:33]([O:35][CH3:36])=[O:34])[CH:8]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-:32])=[O:31])[CH:25]=2)[C:9]=1[C:10]([O:12][CH2:13][C:14]([CH3:22])([CH3:23])[CH2:15][N:16]1[CH2:17][CH2:18][N:19]([C:50]([C:46]2[O:45][CH:49]=[CH:48][CH:47]=2)=[O:51])[CH2:20][CH2:21]1)=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 23044966HCID 23044966, compound

Product 1

HCID 17766916HCID 17766916, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.73 g of 3-(1-piperazinyl)-2,2-dimethylpropyl methyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate dihydrochloride was dissolved in 5 ml of tetrahydrofuran, and 0.6 ml of triethylamine and 0.13 ml of 2-furoyl chloride were added; the mixture was then stirred for 10 minutes while cooling with ice. After evaporating the solvent, the residue was purified by the chromatography method [20 g silica gel, n-hexane:ethyl acetate (2:5)] to give 0.4 g of an oily substance. This oily substance was dissolved in diethyl ether; a slightly excessive amount of a solution of hydrogen chloride in ethanol was added; the solid which separated was collected by filtration to give 0.42 g of the subject compound (yield: 52%). The IR and NMR data of the compound thus obtained are as follows: ##STR12##

Workup

  1. temperaturewhile cooling with ice
  2. customAfter evaporating the solvent
  3. customthe residue was purified by the chromatography method [20 g silica gel, n-hexane:ethyl acetate (2:5)]
  4. customto give 0.4 g of an oily substance
  5. customthe solid which separated
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4cbbcc40932b44b490eb4e314ef78220
Source dataset
uspto-grants-1990_06
Patent number
US04937242

Reaction notes

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