Dimethylformamide → N-(1-benzyl-4-piperidyl)-6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxamide

HRID 329730

反応式

HRID 329730 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.N[CH:23]1[CH2:28][CH2:27][CH2:26][N:25]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:24]1.C(=O)([O-])O.[Na+].C[N:42](C)C=O>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:29]([N:25]1[CH2:26][CH2:27][CH:28]([NH:42][C:13]([C:4]2[C:5]3[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=3[CH:12]=[C:2]([Cl:1])[CH:3]=2)=[O:15])[CH2:23][CH2:24]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

9

反応物 5

HCID 6228DimethylformamideHCID 10928Ethyl chloroformateHCID 4216941-Benzylpiperidin-3-amineHCID 516892Sodium BicarbonateHCID 147198366-Chloro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid

生成物 1

HCID 14719844N-(1-benzyl-4-piperidyl)-6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxamide

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 4.5 g of 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 100 ml of tetrahydrofuran and 10 ml of dimethylformamide is cooled to below 0° C. and 2.5 ml of triethylamine is added under stirring thereto. Further, 2.4 g of ethyl chlorocarbonate is added and the mixture is stirred while keeping below 50° C. for an hour. To the resultant mixture is added 3.6 g of 3-amino-1benzylpiperidine 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-ethyl acetate to give N-(1-benzyl-4-piperidyl) -6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxamide, melting at 203°-206° C.

後処理

  1. stirringthe mixture is stirred
  2. waitwhile keeping below 50° C. for an hour
  3. stirringthe mixture stirred for 4 hours
  4. additionare added
  5. customThe organic layer is separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent is distilled off
  9. customthe residue is recrystallized from ethanol-ethyl acetate

出典と根拠

ORDレコード
ord-e603d9f08ec24ad28c6d4507c3b1bd4b
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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