Diethyl Ether → methyl N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate

HRID 622733Notes

Reaction equation

HRID 622733 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH2:24][CH2:25]Cl)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[C:28]1([CH:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:35][CH2:36][NH2:37])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(OCC)C>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH2:24][CH2:25][NH:37][CH2:36][CH2:35][CH:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 796983,3-DiphenylpropylamineHCID 30168882-Chloroethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

Product 1

HCID 10769981methyl N-(3,3-diphenylpropyl)-2-aminoethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylateYield 40.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution comprising 5.92 g of methyl 2-chloroethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate and 9.50 g of 3,3-diphenylpropylamine in 20 ml of xylene was refluxed under stirring for 105 minutes. The mixture was then cooled. By dilution with diethyl ether a semisolid compound was obtained, and it was separated from the liquid by decantation. The residue was treated with diethyl ether at 0°-4° C. and the supernatant was decanted. This procedure was repeated until a solid was obtained, and this was collected by filtration. Mother liquors and washings from the decantation were collected and evaporated to dryness under vacuum. The residue was chromatographed on a silica gel column (270 g) using a mixture of chloroform and acetone as eluent. Pure fractions were combined and the solvent was evaporated off. The residue was dissolved in diethyl ether and hydrogen chloride in diethyl ether was added. The solid (3.92 g) was crystallized from ethyl acetate or isopropyl acetate and recrystallized from ethyl acetate to give 3.46 g of the title compound, m.p. 128°-132° C.

Workup

  1. temperaturewas refluxed
  2. temperatureThe mixture was then cooled
  3. customit was separated from the liquid by decantation
  4. additionThe residue was treated with diethyl ether at 0°-4° C.
  5. customthe supernatant was decanted
  6. customwas obtained
  7. filtrationthis was collected by filtration
  8. customMother liquors and washings from the decantation were collected
  9. customevaporated to dryness under vacuum
  10. customThe residue was chromatographed on a silica gel column (270 g)
  11. additiona mixture of chloroform and acetone as eluent
  12. customthe solvent was evaporated off
  13. dissolutionThe residue was dissolved in diethyl ether
  14. additionhydrogen chloride in diethyl ether was added
  15. customThe solid (3.92 g) was crystallized from ethyl acetate or isopropyl acetate
  16. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f1af724eb25e4ac692f73ebd3fa6fa85
Source dataset
uspto-grants-1988_09
Patent number
US04772621

Reaction notes

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