3-Phenylprop-2-enoyl chloride → HCID 53757276, compound

HRID 1165830Notes

Reaction equation

HRID 1165830 reaction equation
[C:1](Cl)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:12]([N:19]1[CH2:26][CH:25]2[C:27]([CH3:29])([CH3:28])[CH:21]([CH2:22][NH:23][CH2:24]2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl.O>[C:1]([N:23]1[CH2:24][CH:25]2[C:27]([CH3:29])([CH3:28])[CH:21]([CH2:20][N:19]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:26]2)[CH2:22]1)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 660233-Phenylprop-2-enoyl chlorideHCID 14369013HCID 14369013, compound

Product 1

HCID 53757276HCID 53757276, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3.9 g cinnamic acid chloride were dissolved in 20 ml dichloromethane, and to this solution a solution of 5.5 g 3-benzyl-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane in 10 ml dichloromethane was added with ice cooling. Subsequently the reaction mixture was stirred for 3 hours at room temperature. Then, for working up, the solvent was distilled off and the residue containing the 7-cinnamyl-3-benzyl-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane which had formed was dissolved in water. To remove non-basic fractions, extraction was carried out using ethyl acetate. Then the aqueous phase was made alkaline with dilute sodium hydroxide solution, and the reaction product was extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate, filtered, and the solvent was distilled off. 5 g 7-cinnamoyl-3-benzyl-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane were obtained as a residue.

Workup

  1. distillationthe solvent was distilled off
  2. additionthe residue containing the 7-cinnamyl-3-benzyl-9,9-dimethyl-3,7-diazabicyclo[3,3,1]nonane which
  3. customhad formed
  4. customTo remove non-basic
  5. extractionfractions, extraction
  6. extractionthe reaction product was extracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. dry with materialwas dried over magnesium sulfate
  9. filtrationfiltered
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c01abc801b8242d39215ee9328aa5f81
Source dataset
uspto-grants-1990_03
Patent number
US04912113

Reaction notes

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