2-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoate → 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate

HRID 1087643Notes

Reaction equation

HRID 1087643 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[CH:7]=[C:8]([P:12]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:9]([CH3:11])=O)([O-:3])=[O:2].[CH2:22]([N:29]([CH2:31][CH2:32][O:33][C:34](=[O:39])/[CH:35]=[C:36](\[NH2:38])/[CH3:37])[CH3:30])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)(C)C>[CH3:37][C:36]1[NH:38][C:9]([CH3:11])=[C:8]([P:12]2(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:7]([C:6]2[CH:19]=[CH:20][CH:21]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:35]=1[C:34]([O:33][CH2:32][CH2:31][N:29]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:30])=[O:39]

Participants

4

Reactant 2

HCID 125291882-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoateHCID 540679512-(1-(3-Nitrobenzylidene)acetonyl)-2-oxo-1,3,2-dioxaphosphorinane

Product 1

HCID 136045572-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylateYield 59.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3.11 grams of 2-(1-(3-nitrobenzylidene)-acetonyl)-2-oxo-1,3,2-dioxaphosphorinane and 2.48 grams of 2 -(N-benzyl-N-methylamino)ethyl3-aminocrotonate was dissolved in 30 ml of isopropanol and the mixture was heated to reflux for eight hours. The reaction solution was concentrated in vacuo and the residue was purified by subjecting to a column chromatography (silica gel, n-hexane-ethyl acetate). The resulting pale yellow oil (3.8 grams) was crystallized with ether and recrystallized from a mixture of ethyl acetate and ether to give 3.2 grams of 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(3-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan- 2-yl)-1,4-dihydropyridine-3-carboxylate, pale yellow crystals, m.p. 139°-40° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for eight hours
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customthe residue was purified
  5. customThe resulting pale yellow oil (3.8 grams) was crystallized with ether
  6. customrecrystallized from a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-cebe0f14f78043ea8b0bbe32e27dc24b
Source dataset
uspto-grants-1991_07
Patent number
US05036059

Reaction notes

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