Methyl Isobutyl Ketone → (E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate

HRID 359403

Reaction equation

HRID 359403 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[CH2:15][CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:24](=[O:27])([O-:26])[O-].[Na+].[Na+].CC(C)CC(=O)C>O>[C:9]([OH:11])(=[O:10])[C:24]([OH:26])=[O:27].[CH3:1][N:2]([CH2:15]/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 10340Sodium CarbonateHCID 94242Benzene, (3-chloro-1-propenyl)-HCID 110631401-Piperidinecarboxylic acid, 4-(methylamino)-, ethyl ester

Product 1

HCID 86744664(E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 14 parts of ethyl 4-(methylamino)-1-piperidinecarboxylate, 13 parts of (3-chloro-1-propenyl)benzene, 26.5 parts of sodium carbonate and 240 parts of 4-methyl-2-pentanone was stirred and refluxed over week-end using a water separator. The reaction mixture was cooled, water was added and the layers were separated. The organic phase was dried, filtered and evaporated. The residue was converted into the ethanedioate salt in 2-propanol and 2-propanone. The salt was filtered off and dried, yielding 23.4 parts of (E)-ethyl 4-[methyl(3-phenyl-2-propenyl)amino]-1-piperidinecarboxylate ethanedioate (1:1); mp. 160.2° C. (intermediate 3).

Workup

  1. temperaturerefluxed over week-end
  2. temperatureThe reaction mixture was cooled
  3. customthe layers were separated
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt was filtered off
  8. customdried

Sources & evidence

ORD record
ord-d87e7e260dca4cde833a50446bf66915
Source dataset
uspto-grants-1991_03
Patent number
US05001125

Linked notes

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