Hydrochloric Acid → 2,2-Dimethyl-3-[4-(prop-2-en-1-yl)piperazin-1-yl]propyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate--hydrogen chloride (1/2)

HRID 2107959Notes

Reaction equation

HRID 2107959 reaction equation
[ClH:1].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.[CH2:45]([Cl:48])[CH:46]=[CH2:47].Cl>O1CCCC1.C(OCC)C.C(O)C>[ClH:48].[ClH:1].[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]([CH2:47][CH:46]=[CH2:45])[CH2:20][CH2:21]1)=[O:11]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7850Allyl chlorideHCID 8471TriethylamineHCID 23044966HCID 23044966, compound

Product 1

HCID 1640312,2-Dimethyl-3-[4-(prop-2-en-1-yl)piperazin-1-yl]propyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate--hydrogen chloride (1/2)Yield 75%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

1.5 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 10 ml of tetrahydrofuran, and 1.2 ml of triethylamine and 0.22 ml of allyl chloride were added. The mixture was then stirred at 50° C. for 12 hours. After evaporating the solvent, the residue was purified by the chromatography method [20 g silica gel, eluted with ethyl acetate] to give 1.1 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, after which it was recrystallized from ethanol to thereby give 1.1 g of the subject compound (yield: 75%). The IR and NMR data of the compound thus obtained are as follows: ##STR13##

Workup

  1. customAfter evaporating the solvent
  2. customthe residue was purified by the chromatography method [20 g silica gel, eluted with ethyl acetate]
  3. customto give 1.1 g of an oily substance
  4. customthe solid which separated
  5. filtrationwas collected by filtration
  6. customafter which it was recrystallized from ethanol

Sources & evidence

ORD record
ord-6509c2b044fe41af89b18df9fe8470a6
Source dataset
uspto-grants-1990_06
Patent number
US04937242

Reaction notes

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