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

HRID 329733

反応式

HRID 329733 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][CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:35]1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([NH:19][CH:39]2[CH2:38][CH2:37][N:36]([CH2:40][CH2:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:35][CH2:34]2)=[O:17])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[N:7]([CH3:13])[C:6]=2[CH:14]=1

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 145172346-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acidHCID 198711523-Amino-1-(3-phenylpropyl)piperidine

生成物 1

HCID 198711756-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-N-[1-(3-phenylpropyl)-4-piperidyl]-2H-1,4-benzoxazine-8carboxamide 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 45 minutes. To the resultant mixture is added 3.77 g of 3-amino-1-(3-phenylpropyl)piperidine and the mixture stirred for 3 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 ethnnolic hydrochloric acid to give 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-N-[1-(3-phenylpropyl)-4-piperidyl]-2H-1,4-benzoxazine-8carboxamide hydrochloride, melting at 174°-176° C. with decomposition.

後処理

  1. stirringthe mixture is stirred at the same temperature for 45 minutes
  2. stirringthe mixture stirred for 3 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 ethnnolic hydrochloric acid

出典と根拠

ORDレコード
ord-c4714057396c4404810cb3a5185f4383
出典データセット
uspto-grants-1990_01
特許番号
US04892872

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