Piperidine → HCID 54488795, compound

HRID 2166697Notes

Reaction equation

HRID 2166697 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH3:3].[CH2:13]([O:15][C:16](=[O:21])[CH2:17]C([O-])=O)[CH3:14].N1CCCCC1>N1C=CC=CC=1>[CH3:1][N:2]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:17][C:16]([O:15][CH2:13][CH3:14])=[O:21])=[CH:7][CH:6]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 1932514-DimethylaminomethylbenzaldehydeHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 54488795HCID 54488795, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-dimethylaminomethylbenzaldehyde (32.64 g), monoethylmalonate (29.07 g), pyridine (100 ml) and piperidine (2 ml) were heated under reflux with stirring for 5 hr. The pyridine was evaporated at reduced pressure, and the oily residue was extracted with diethyl ether. The combined ether extracts were washed with water and dried over magnesium sulphate. The ether was evaporated at reduced pressure to yield ethyl 4-(dimethylaminomethyl)cinnamate as a light straw coloured oil (46.57 g).

Workup

  1. temperaturewere heated
  2. temperatureunder reflux
  3. customThe pyridine was evaporated at reduced pressure
  4. extractionthe oily residue was extracted with diethyl ether
  5. washThe combined ether extracts were washed with water
  6. dry with materialdried over magnesium sulphate
  7. customThe ether was evaporated at reduced pressure

Sources & evidence

ORD record
ord-347b786f267e4d60a252c20cbc8ca0d6
Source dataset
uspto-grants-1983_06
Patent number
US04388317

Reaction notes

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