Diethylamine → 7-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate

HRID 1193850

Reaktionsgleichung

Reaktionsgleichung von HRID 1193850
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14]Cl)[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH2:18]([NH:20][CH2:21][CH3:22])[CH3:19].C([O:25][C:26](=[O:28])C)C.[CH3:29][OH:30].[OH-:31].[NH4+]>C(O)C>[C:26]([OH:28])(=[O:25])[C:29]([OH:31])=[O:30].[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14][N:20]([CH2:21][CH3:22])[CH2:18][CH3:19])[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 8021Diethylamine3×HCID 14923Ammonium HydroxideHCID 137264457-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-oneHCID 21584119Ethylacetate methanol

Produkt 1

HCID 137265987-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspension 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 2.26 ml (0.022 mole) of diethylamine and the mixture heated to reflux. (Complete dissolution occurred). After 1 hr, another 2.26 ml (0.022 mole) of diethylamine was added followed by 5.0 ml (0.049 mole) and heating continued for 2 more hours. TLC (ethylacetate/methanol/conc. ammonium hydroxide, 7:2:1, v/v/v) still showed presence of starting material; another 2.26 ml (0.022 mole) of diethylamine was added and heating continued for 15 hr at reflux. Solvent was removed by rotary evaporation (60° C., 30 mm Hg) and the residue taken up in methylene chloride, washed twice with dilute aqueous sodium hydroxide and once with water. The organic layer was dried over sodium sulfate, filtered and concentrated by rotary evaporation, and azeotroped once with toluene. The oil was treated with oxalic acid in isopropyl alcohol which yielded 6.7 g (76%) of white crystals, m.p. 163°-164° C.

Aufarbeitung

  1. temperaturethe mixture heated to reflux
  2. dissolution(Complete dissolution occurred)
  3. temperatureheating
  4. temperatureheating
  5. waitcontinued for 15 hr
  6. temperatureat reflux
  7. customSolvent was removed by rotary evaporation (60° C., 30 mm Hg)
  8. washwashed twice with dilute aqueous sodium hydroxide and once with water
  9. dry with materialThe organic layer was dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated by rotary evaporation
  12. customazeotroped once with toluene
  13. additionThe oil was treated with oxalic acid in isopropyl alcohol which

Quellen und Nachweise

ORD-Eintrag
ord-4005129756644a39acf3a294a465b06f
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810795

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