Water → N-(1-Benzyl-4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide

HRID 260885

反応式

HRID 260885 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:15]([N:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[CH3:19])(=[O:17])[CH3:16].C([O-])(=O)C.[Na+].O>C(O)C>[CH2:8]([N:5]1[CH2:6][CH2:7][CH:2]([NH:1][S:26]([C:23]2[CH:22]=[CH:21][C:20]([N:18]([C:15](=[O:17])[CH3:16])[CH3:19])=[CH:25][CH:24]=2)(=[O:28])=[O:27])[CH2:3][CH2:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 962WaterHCID 2931464-(N-methylacetamido)benzene-1-sulfonyl chlorideHCID 4158521-Benzyl-4-piperidylamineHCID 517045Sodium Acetate

生成物 1

HCID 15049722N-(1-Benzyl-4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Amino-1-benzylpiperidine (3.63 ml, 17.8 mmol) was added to a suspension of the 4-(N-acetyl-N-methylamino)benzenesulfonyl chloride (4.00 g, 16.2 mmol) prepared in Preparative Example 12 and sodium acetate (2.65 g) in ethanol (40 ml). The obtained mixture was stirred at room temperature for 4 hours, followed by the addition of water. The obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of common salt, dried over magnesium sulfate, and concentrated to give N-(1-benzyl-4-piperidyl)-4-(N-acetyl-N-methylamino)benzenesulfonamide as a colorless viscous oil. This oil was dissolved in 4N aqueous hydrochloric acid and the obtained solution was heated under reflux for 3 hours. The resulting mixture was concentrated to give a solid residue. This residue was recrystallized from ethyl acetate to give the title compound as a white crystal (highly hygroscopic one) (5.80 g, overall yield of two steps: 80%).

後処理

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of common salt, dried over magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-59f0bf73917b49ef973df62ce5363411
出典データセット
uspto-grants-1996_06
特許番号
US05530118

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