Methyl 2-[4-(aminomethyl)phenyl]benzoate → 6-Carbethoxymethyliden-1-[4-(2-carbomethoxyphenyl)benzyl]-4,4-dimethylpiperidin-2-one

HRID 5863Notes

Reaction equation

HRID 5863 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1)([O:3][CH3:4])=[O:2].[C:19](/[CH:24]=[C:25]1\[CH2:26][C:27]([CH3:33])([CH3:32])[CH2:28][C:29](O\1)=[O:30])([O:21][CH2:22][CH3:23])=[O:20]>C1(C)C=CC=CC=1>[C:19]([CH:24]=[C:25]1[N:16]([CH2:15][C:14]2[CH:13]=[CH:12][C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:1]([O:3][CH3:4])=[O:2])=[CH:18][CH:17]=2)[C:29](=[O:30])[CH2:28][C:27]([CH3:32])([CH3:33])[CH2:26]1)([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 1393434Methyl 2-[4-(aminomethyl)phenyl]benzoateHCID 13081244(E)-5-Carbethoxymethylidene-3,3-dimethylvalerolactone

Product 1

HCID 540740746-Carbethoxymethyliden-1-[4-(2-carbomethoxyphenyl)benzyl]-4,4-dimethylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound (i) of Example 9 (1.2 g, 0.005 mole) and compound (b) of Example 2 (1.1 g, 0.005 mole) are combined in toluene (50 mL) and refluxed for 5 hours. The toluene is removed in vacuo and the residue is chromatographed on silica gel using hexane/ethyl acetate as the mobile phase. The title compound is isolated as a colorless oil (1.2 g, 52%). Mass Spec. (DCI) m/z 436 (M+H). Analysis--calc'd for C26H29NO5 : C, 70.96; H, 6.76; N, 3.18; found: C, 70.76; H, 7.11; N, 2.77.

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe toluene is removed in vacuo
  3. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-ca5895282f2f46f58e9c9d3bbfc13aa0
Source dataset
uspto-grants-1993_09
Patent number
US05246940

Reaction notes

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