3-Phenylprop-2-Enal → HCID 66987718, compound

HRID 555975Notes

Reaction equation

HRID 555975 reaction equation
[CH3:1]/[CH:2]=[C:3]1\[C@H:4]2[CH:11]=[C:10]([CH3:12])[CH2:9][C@@:8]\1([NH2:13])[C:7]1[CH:14]=[CH:15][C:16]([NH:18][C:6]=1[CH2:5]2)=[O:17].[CH:19](=O)[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C.C1COCC1>[C:22]1([CH:21]=[CH:20][CH:19]=[N:13][C@@:8]23[C:7]4[CH:14]=[CH:15][C:16](=[O:17])[NH:18][C:6]=4[CH2:5][C@@H:4](/[C:3]/2=[CH:2]\[CH3:1])[CH:11]=[C:10]([CH3:12])[CH2:9]3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 9794806HCID 9794806, compound

Product 1

HCID 66987718HCID 66987718, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

20 mg Huperzine A, and 77 mg cinnamaldehyde were refluxed in 2 mL isopropanol for 3 hours. Solvent was removed under vacuum. The crude reaction mixture was dissolved in 3 mL anhydrous THF and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H).

Workup

  1. customSolvent was removed under vacuum
  2. customThe crude reaction mixture
  3. custompurified with prep

Sources & evidence

ORD record
ord-daabc654b2c64a11a4837e1db0950023
Source dataset
uspto-grants-2011_11
Patent number
US08053577B2

Reaction notes

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