Ethyl chloroformate → 6-chloro-3,4-dihydro-3-oxo-N-(3quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride

HRID 329723

반응식

HRID 329723 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=O)[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.C(Cl)(=O)OCC.[NH2:22][CH:23]1[CH:28]2[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]2)[CH2:24]1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:22][CH:23]2[CH:28]3[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]3)[CH2:24]2)=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1

참가 물질

8

반응물 4

HCID 10928Ethyl chloroformateHCID 1232383-AminoquinuclidineHCID 516892Sodium BicarbonateHCID 147198366-Chloro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid

생성물 1

HCID 198711296-chloro-3,4-dihydro-3-oxo-N-(3quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 4.6 g of 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 50 ml of tetrahydrofuran is cooled to below 0° C. and 5 ml of triethylamine is added under stirring thereto. Further, 2.5 g of ethyl chlorocarbonate is added and the mixture is stirred for an hour. To the resultant mixture is added 3.0 g of 3-aminoquinuclidine 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-water followed by treating with ethanolic hydrochloric acid to give 6-chloro-3,4-dihydro-3-oxo-N-(3quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 227°-229° C.

후처리

  1. stirringthe mixture is stirred for an hour
  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-water
  9. additionby treating with ethanolic hydrochloric acid

출처 및 근거

ORD 기록
ord-45b25457a3d34756be11f22b9cf9f7fe
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892872

연결된 노트

불러오는 중…