Pyridine → HCID 19868647, compound

HRID 330486Notes

Reaction equation

HRID 330486 reaction equation
C(O[C:5]1[CH:20]=[C:19]([O:21][C:22](=[O:24])[CH3:23])[C:8]2[C:9]([CH3:18])=[C:10]3[N:15]([C:16](=[O:17])[C:7]=2[CH:6]=1)[CH2:14][CH2:13][CH2:12][CH2:11]3)(=O)C.[C:25]([O:28]C(=O)C)(=[O:27])[CH3:26].N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:25]([O:28][C:20]1[CH:5]=[CH:6][C:7]2[C:16](=[O:17])[N:15]3[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]3)[C:9](=[CH2:18])[C:8]=2[C:19]=1[O:21][C:22](=[O:24])[CH3:23])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14791786HCID 14791786, compound

Product 1

HCID 19868647HCID 19868647, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Reflux crude 8,10-bis(acetyloxy)-1,2,3,4-tetrahydro-11-methyl-6H-benzo[b]quinolizin-6-one (11.8 g), acetic anhydride (20.2 ml), pyridine (20.2 ml), and chloroform (400 ml) for 20 hrs. Concentrate the cooled solution to dryness, and dilute the residue with ethyl acetate. Separate the resulting crystals by filtration, and concentrate the mother liquor. Chromatograph the residue over silica gel, and elute the column with 10% ethyl acetate in dichloromethane. Combine and concentrate fractions, and crystallize to obtain 9,10-bis(acetyloxy)-1,2,3,4,11,11a-hexahydro-11-methylene-6H-benzo[b]quinolizin-6-one, m.p. 129°-132° C. (from CHCl3 -EtOAc).

Workup

  1. concentrationConcentrate the cooled solution to dryness
  2. additiondilute the residue with ethyl acetate
  3. customSeparate the resulting crystals
  4. filtrationby filtration
  5. concentrationconcentrate the mother liquor
  6. washelute the column with 10% ethyl acetate in dichloromethane
  7. concentrationCombine and concentrate fractions
  8. customcrystallize

Sources & evidence

ORD record
ord-28f72cd4d14e495898a9c65ed03d7b30
Source dataset
uspto-grants-1990_01
Patent number
US04897391

Reaction notes

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