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

HRID 1419571노트

반응식

HRID 1419571 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-a0d79106bb7c4f3b8324fbe84cfddad2
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05885999

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