4-Methylmorpholine → N-(1-benzyl-4-piperidyl)-6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride

HRID 329731

Reaktionsgleichung

Reaktionsgleichung von HRID 329731
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=2[CH:14]=1.C[N:19]1CCOCC1.C(Cl)(=O)OCC(C)C.N[CH:34]1[CH2:39][CH2:38][CH2:37][N:36]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:35]1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[ClH:1].[CH2:40]([N:36]1[CH2:37][CH2:38][CH:39]([NH:19][C:15]([C:4]2[C:5]3[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=3[CH:14]=[C:2]([Cl:1])[CH:3]=2)=[O:17])[CH2:34][CH2:35]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4216941-Benzylpiperidin-3-amineHCID 516892Sodium BicarbonateHCID 145172346-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid

Produkt 1

HCID 19871182N-(1-benzyl-4-piperidyl)-6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4.0 g of 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 80 ml of tetrahydrofuran is cooled to below 0° C. and 3.17 g of N-methylmorpholine is added under stirring thereto. Further, 2.35 g of isobutyl chlorocarbonate is added and the mixture is stirred at the same temperature for an hour. To the resultant mixture is added 3.28 g of 3-amino-1-benzylpiperidine and the mixture stirred for 4 hours. After completion of the reaction, aqueous sodium hydrogen carbonate and ethyl acetate are added. The organic layer is separated, washed with water and dried over magnesium sulfate. The solvent is distilled off and the residue is recrystallized from ethanol followed by treating with ethanolic hydrochloric acid to give N-(1-benzyl-4-piperidyl)-6-chloro-3,4-dihydro-2,4-dimethyl- 3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 214° C. with decomposition.

Aufarbeitung

  1. stirringthe mixture is stirred at the same temperature for an hour
  2. stirringthe mixture stirred for 4 hours
  3. additionare added
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe residue is recrystallized from ethanol
  9. additionby treating with ethanolic hydrochloric acid

Quellen und Nachweise

ORD-Eintrag
ord-f24871f2bc754110a2ce57f66d19cebf
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892872

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