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

HRID 329732

반응식

HRID 329732 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.CN1CCOCC1.C(Cl)(=O)OCC(C)C.[NH2:33][CH:34]1[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:36][CH2:35]1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[OH2:10].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:15]([NH:33][CH:34]2[CH2:39][CH2:38][N:37]([CH2:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:36][CH2:35]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

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 107287881-(2-Phenylethyl)piperidin-4-amineHCID 145172346-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid

생성물 1

HCID 198711616-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-N-[1-(2-phenylethyl)-4-piperidyl]-2H-1,4-benzoxazine-8-carboxamide hydrochloride monohydrate

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 45 minutes. To the resultant mixture is added 3.52 g of 4-amino-1-(2-phenylethyl)piperidine and the mixture stirred for 2 hours. After completion of the reaction, aqueous sodium hydrogen carbonate and ethyl acetate are added. The organic layer is separated, and diluted hydrochloric acid is added thereto. The precipitated crystals are collected by filtration and recrystallized from ethanol to give 6-chloro-3,4-dihydro-2,4-dimethyl-3-oxo-N-[1-(2-phenylethyl)-4-piperidyl]-2H-1,4-benzoxazine-8-carboxamide hydrochloride monohydrate, melting at 257°-259° C. with decomposition.

후처리

  1. stirringthe mixture is stirred at the same temperature for 45 minutes
  2. stirringthe mixture stirred for 2 hours
  3. additionare added
  4. customThe organic layer is separated
  5. additiondiluted hydrochloric acid is added
  6. filtrationThe precipitated crystals are collected by filtration
  7. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-8caa4c95bc7b45b28f4042186128afc7
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892872

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