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

HRID 329723

反応式

HRID 329723 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45b25457a3d34756be11f22b9cf9f7fe
出典データセット
uspto-grants-1990_01
特許番号
US04892872

関連ノート

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