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

반응식

HRID 329731 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f24871f2bc754110a2ce57f66d19cebf
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892872

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