Benzylamine → Ethyl 3-(benzylamino)-3-oxopropanoate

HRID 977951Notes

Reaction equation

HRID 977951 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12]([CH2:14][C:15](Cl)=[O:16])=[O:13])[CH3:10]>C(Cl)Cl>[CH2:1]([NH:8][C:15]([CH2:14][C:12]([O:11][CH2:9][CH3:10])=[O:13])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 118931Ethyl 3-chloro-3-oxopropionate

Product 1

HCID 11379032Ethyl 3-(benzylamino)-3-oxopropanoateYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of benzylamine (43.24 g) and methylene chloride (300 ml) is cooled with ice-water, and a solution of ethoxycarbonylacetyl chloride (29.63 g) in methylene chloride (150 ml) is added dropwise thereto. The mixture is stirred at the same temperature for 2 hours. The mixture is filtered to remove precipitates (benzylamine hydrochloride). The filtrate is washed with 2% hydrochloric acid and a saturated sodium chloride solution, dried and then evaporated to remove the solvent. The residue is recrystallized from a mixture of ether and n-hexane, whereby ethyl (N-benzylcarbamoyl)acetate (42.15 g) is obtained as colorless needles. Yield: 96.8%.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove
  3. customprecipitates (benzylamine hydrochloride)
  4. washThe filtrate is washed with 2% hydrochloric acid
  5. dry with materiala saturated sodium chloride solution, dried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is recrystallized from a mixture of ether and n-hexane

Sources & evidence

ORD record
ord-59c71ced066e4c229159e133abe1bcf9
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

Loading…