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

HRID 1419571Notes

Reaction equation

HRID 1419571 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-a0d79106bb7c4f3b8324fbe84cfddad2
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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