Oxalic Acid → 7-Chloro-2,3-dihydro-4-methyl-2-[2-methyl(phenylmethyl)amino]pyrido[3,2-f][1,4]oxazepin-5(4H)-one oxalate

HRID 1194255Notes

Reaction equation

HRID 1194255 reaction equation
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8](CCCl)[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH2:18]([CH2:25][NH2:26])[C:19]1C=C[CH:22]=[CH:21][CH:20]=1.[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>C(O)C.C(O)(C)C>[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([NH:26][CH2:25][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:27]=3[CH3:28])[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 1001Phenethylamine2×HCID 137264457-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one

Product 1

HCID 212715447-Chloro-2,3-dihydro-4-methyl-2-[2-methyl(phenylmethyl)amino]pyrido[3,2-f][1,4]oxazepin-5(4H)-one oxalateYield 47.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 6.0 g (0.022 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 5.3 g (0.044 mole) of benzylmethylamine and the mixture heated to reflux for three days. The solvent was removed by rotary evaporation, and the residue was taken up in 100 ml of methylene chloride, which was subsequently washed with 2×50 ml of dilute sodium hydroxide and 50 ml water, dried over sodium sulfate, filtered, and concentrated by rotary evaporation. Residual benzylmethylamine was removed at 95° C., 0.5 mm Hg. However, the mass spectrum now showed starting material; therefore, the residue was taken up in 50 ml of absolute ethanol. To the resulting solution was added 2.7 g (0.022 mole) of benzylmethylamine and the mixture heated to reflux for 24 hrs. The reaction mixture was subjected to the same work-up as mentioned before. The syrup was treated with oxalic acid in isopropyl alcohol. The resulting crystals were recrystallized from ethanol/isopropyl alcohol to give 4.7 g (47.9%) of white crystals, m.p. 176°-179° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for three days
  3. customThe solvent was removed by rotary evaporation
  4. washwhich was subsequently washed with 2×50 ml of dilute sodium hydroxide and 50 ml water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customResidual benzylmethylamine was removed at 95° C.
  9. temperaturethe mixture heated
  10. temperatureto reflux for 24 hrs
  11. customThe resulting crystals were recrystallized from ethanol/isopropyl alcohol

Sources & evidence

ORD record
ord-a9e2663b97224780af0be7ea34a58f20
Source dataset
uspto-grants-1989_03
Patent number
US04812565

Reaction notes

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