Benzenepropanal → HCID 67279793, compound

HRID 1692609Notes

Reaction equation

HRID 1692609 reaction equation
[N:1]1([C:7]2[CH:8]=[CH:9][C:10]3[CH2:11][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:14][O:15][C:16]=3[N:17]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[C:25]1([CH2:31][CH2:32][CH:33]=O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH-].[Na+]>C1COCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[C:25]1([CH2:31][CH2:32][CH2:33][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[CH:9][C:10]4[CH2:11][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:14][O:15][C:16]=4[N:17]=3)[CH2:2][CH2:3]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7707BenzenepropanalHCID 14798Sodium HydroxideHCID 67279638HCID 67279638, compound

Product 1

HCID 67279793HCID 67279793, compoundYield 4%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To the compound (0.10 g) obtained in Example 33, step 1 and 3-phenylpropanal (118 μL) was added titanium tetraisopropoxide (664 μL), and the mixture was stirred at room temperature for 18 hr under a nitrogen atmosphere. A solution of poly(methylhydrosilane) (106 μL) in THF (5 mL) was added, and the mixture was stirred at room temperature for 3 hr. A 3N aqueous sodium hydroxide solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (solvent gradient; 10→40% ethyl acetate/hexane) to give tert-butyl 8-[4-(3-phenylpropyl)piperazin-1-yl]-2,3-dihydropyrido[3,2-f][1,4]oxazepine-4(5H)-carboxylate (0.02 g, 4%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (solvent gradient; 10→40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f637b497d7624fc6a9eb2c891021a7c3
Source dataset
uspto-grants-2012_04
Patent number
US08158617B2

Reaction notes

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