Benzylamine → HCID 429236, compound

HRID 905120Notes

Reaction equation

HRID 905120 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C1C=CC=CC=1>[CH2:1]([NH:8][CH:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 69637Diethyl bromomalonate

Product 1

HCID 429236HCID 429236, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Benzylamine (18.3 g) and diethyl bromomalonate (20.3 g) were dissolved in dry benzene (100 ml), and the mixture was heated under reflux for 14 hours with stirring. The precipitated salt was removed by filtration from the reaction mixture. The filtrate was washed with dilute hydrochloric acid to remove the unreacted benzylamine. The benzene layer was washed with water three times, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography using hexane/ethyl acetate (4:1) as an eluent to give 4.7 g (yield 21%) of diethyl benzylaminomalonate having the following NMR data.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. customThe precipitated salt was removed by filtration from the reaction mixture
  4. washThe filtrate was washed with dilute hydrochloric acid
  5. customto remove the unreacted benzylamine
  6. washThe benzene layer was washed with water three times
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c5afdae08b6483ab92970860bcc30e2
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

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