Homoveratrylamine → HCID 86758565, compound

HRID 356629Notes

Reaction equation

HRID 356629 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:24][CH2:25][NH2:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>C(Cl)Cl>[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:2][C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH2:24][CH2:25][NH-:26])[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]

Participants

4

Reactant 2

HCID 8421HomoveratrylamineHCID 96345tert-Butyl ethyl malonate

Product 1

HCID 86758565HCID 86758565, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15.35 g of monoethyl tert.butyl malonate in 200 ml of anhydrous CH2Cl2 are stirred, at ambient temperature, 15.88 g of N,N'-carbonyldiimidazole in small batches. After 30 minutes, 14.8 g of 2-(3,4-dimethoxyphenyl)ethylamine are added. After a further 15 hours the solvent is distilled off in vacuo. The residue is mixed with 200 ml of water, acidified with 2N HCl and extracted with ethyl acetate. The organic phase is washed with water and concentrated by evaporation after drying over Na2SO4. The residue is triturated with petroleum ether (40° to 60° C.) and brought to crystallisation.

Workup

  1. distillationAfter a further 15 hours the solvent is distilled off in vacuo
  2. additionThe residue is mixed with 200 ml of water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. concentrationconcentrated by evaporation
  6. dry with materialafter drying over Na2SO4
  7. customThe residue is triturated with petroleum ether (40° to 60° C.)
  8. custombrought to crystallisation

Sources & evidence

ORD record
ord-2e3c2824040f41639a9d9e529a942075
Source dataset
uspto-grants-1998_11
Patent number
US05837712

Reaction notes

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