Pyridine → tert-Butyl 4-{2-[(methylsulfonyl)amino]phenyl}piperidinecarboxylate

HRID 1419571ノート

反応式

HRID 1419571 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].N1C=CC=CC=1>ClCCl>[C:6]([O:10][C:11]([N:13]1[CH2:14][CH2:15][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH:25][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

参加物

5

反応物 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 22266191tert-Butyl 4-(2-aminophenyl)piperidine-1-carboxylate

生成物 1

HCID 22266209tert-Butyl 4-{2-[(methylsulfonyl)amino]phenyl}piperidinecarboxylate収率 102.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Methanesulfonyl chloride (364 mg) was added to a solution of 1-t-butoxycarbonyl-4-(2-aminophenyl)piperidine (880 mg) and pyridine (252 mg) in dichloromethane. The mixture was heated under reflux for 30 min., cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was partitioned between aqueous citric acid (10%) and ethyl acetate (100 mL). The organic layer was separated, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a yellow solid (1.15 g), δH (CDCl3) 1.48 (9H, s), 1.60 (2H, m), 1.73 (2H, m), 2.83 (2H, m), 3.04 (3H, s), 3.09 (1H, m), 4.26 (2H, m), 6.21 (1H, br s), 7.21-7.37 (2H, m). m/e (ES+) 355 (MH+).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 30 min.
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was partitioned between aqueous citric acid (10%) and ethyl acetate (100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-a0d79106bb7c4f3b8324fbe84cfddad2
出典データセット
uspto-grants-1999_03
特許番号
US05885999

反応ノート

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