Dimethylamine → 7-Chloro-2-[2-(dimethylamino)ethyl]-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one fumarate

HRID 247348Notes

Reaction equation

HRID 247348 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[C:15]([CH3:16])=[N:14][C:13]2[O:12][CH:11]([CH2:17][CH2:18]Cl)[CH2:10][N:9]([CH3:20])[C:8](=[O:21])[C:7]=2[CH:6]=1.CO.[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28]>C(O)(C)C>[C:24]([OH:31])(=[O:30])/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28].[Cl:4][C:5]1[C:15]([CH3:16])=[N:14][C:13]2[O:12][CH:11]([CH2:17][CH2:18][N:2]([CH3:3])[CH3:1])[CH2:10][N:9]([CH3:20])[C:8](=[O:21])[C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 887MethanolHCID 444972Fumaric AcidHCID 143915077-Chloro-2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one

Product 1

HCID 212715417-Chloro-2-[2-(dimethylamino)ethyl]-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one fumarate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 70 ml of freshly collected dimethylamine was added 5.0 g (0.017 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one and 5 ml of methanol. The reaction flask was sealed tightly and left standing at room temperature for 2 days. The reaction flask was cooled and opened and the solvent evaporated in a stream of air. The residue was taken up in 100 ml of methylene chloride and the solution was washed with 3×50 ml of 1N sodium hydroxide, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residual oil was treated with 2 equivalents of fumaric acid in isopropyl alcohol which yielded 5.3 g (59%) of white analytically pure crystals, m.p. 153°-56° C.

Workup

  1. customThe reaction flask was sealed tightly
  2. waitleft
  3. temperatureThe reaction flask was cooled
  4. customthe solvent evaporated in a stream of air
  5. washthe solution was washed with 3×50 ml of 1N sodium hydroxide
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customyielded 5.3 g (59%) of white analytically pure crystals, m.p. 153°-56° C.

Sources & evidence

ORD record
ord-eee828a1f360489bae9d0aaa91e0adad
Source dataset
uspto-grants-1987_11
Patent number
US04705853

Reaction notes

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