Dimethylamine → 2-[2-(Dimethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepin-5(4H)-one oxalate hydrate

HRID 247312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247312
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[O:12])[C:7]2[CH:13]=[N:14][CH:15]=[CH:16][C:6]=2[O:5]1.[C:17]([OH:22])(=[O:21])[C:18]([OH:20])=[O:19].[CH3:23][NH:24][CH3:25]>C(O)(C)C.O>[OH2:5].[C:17]([OH:22])(=[O:21])[C:18]([OH:20])=[O:19].[CH3:23][N:24]([CH3:25])[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[O:12])[C:7]2[CH:13]=[N:14][CH:15]=[CH:16][C:6]=2[O:5]1

Komponenten

6

Edukt 3

HCID 674Dimethylamine2×HCID 971Oxalic AcidHCID 137264002-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepin-5(4H)-one

Produkt 1

HCID 137264052-[2-(Dimethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepin-5(4H)-one oxalate hydrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A solution of 5 g (0.02 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,4-f][1,4]oxazepin-5(4H)-one, in 25 ml of dimethylamine was placed in a sealed vessel and stirred for 72 hr. The vessel was opened and the excess dimethylamine allowed to evaporate. The residue was dissolved in chloroform and the solvent was stripped off in vacuo to remove excess dimethylamine. The residue was partitioned between dilute sodium hydroxide and ethyl acetate. The ethyl acetate solution was concentrated and the residue was treated with 3 g (0.033 mole) of oxalic acid in 50 ml of isopropyl alcohol and enough water to dissolve the salt while boiling. The resulting crystals were recrystallized from the same solvent. Yield of product was 5.3 g (60%), m.p. 179°-181° C.

Aufarbeitung

  1. customto evaporate
  2. dissolutionThe residue was dissolved in chloroform
  3. customto remove excess dimethylamine
  4. customThe residue was partitioned between dilute sodium hydroxide and ethyl acetate
  5. concentrationThe ethyl acetate solution was concentrated
  6. dissolutionto dissolve the salt
  7. customThe resulting crystals were recrystallized from the same solvent

Quellen und Nachweise

ORD-Eintrag
ord-e6814a9f3e7c43b291f9a12337f83152
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705853

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