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

反応式

HRID 329731 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f24871f2bc754110a2ce57f66d19cebf
出典データセット
uspto-grants-1990_01
特許番号
US04892872

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