Benzaldehyde → 7-Benzylidene-6,7-dihydro-5H-[1]pyrindine

HRID 2212814

Reaction equation

HRID 2212814 reaction equation
[N:1]1[C:9]2[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(OC(=O)C)(=O)C>>[CH:10](=[C:8]1[C:9]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 7918Acetic AnhydrideHCID 68292Pyrindan

Product 1

HCID 674163677-Benzylidene-6,7-dihydro-5H-[1]pyrindineYield 75%

Procedure

15 g (0.125 mol) of 6,7-dihydro-5H-[1]pyrindine, 20.1 g (0.19 mol) of freshly destilled benzaldehyde and 24.5 g (0.24 mol) of acetic acid anhydride were heated under reflux for 24 h. The reaction mixture was evaporated, the residual oil dissolved in methylene chloride, the solution extracted with 1N NaOH solution, and the organic phase dried and evaporated. The residue was destilled under reduced pressure to give 19.3 g (75%) of the title compound.

Workup

  1. temperatureunder reflux for 24 h
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residual oil dissolved in methylene chloride
  4. extractionthe solution extracted with 1N NaOH solution
  5. customthe organic phase dried
  6. customevaporated

Sources & evidence

ORD record
ord-b4246cd9d8eb40b4b6de6d466dbf1014
Source dataset
uspto-grants-2006_09
Patent number
US07105513B2

Linked notes

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