3-Phenylprop-2-Enal → HCID 5963357, compound

HRID 355573Notes

Reaction equation

HRID 355573 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH2:11]([NH:18][CH2:1]/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 3073-Phenylprop-2-EnalHCID 7504BenzylamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 5963357HCID 5963357, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Cinnamaldehyde and benzylamine were dissolved in 1% acetic acid in methanol under an atmosphere of dry nitrogen. Sodium cyanoborohydride (~1 equivalent) was added, and stirring was continued for 18 hours at which time the solvent was removed under reduced pressure. The residue was suspended in ether, washed with 5% NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound.

Workup

  1. customthe solvent was removed under reduced pressure
  2. washwashed with 5% NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2efe3411acab4b02881ed75c9f8f565c
Source dataset
uspto-grants-1998_11
Patent number
US05831115

Reaction notes

Loading…