Methyl iodide → N-[2-(1-t-Butoxycarbonylpiperidin-4-yl)phenyl]-N-methylmethanesulfonamide

HRID 1419573Notes

Reaction equation

HRID 1419573 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:27]I>O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22266209tert-Butyl 4-{2-[(methylsulfonyl)amino]phenyl}piperidinecarboxylate

Product 1

HCID 67553893N-[2-(1-t-Butoxycarbonylpiperidin-4-yl)phenyl]-N-methylmethanesulfonamideYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 73.4 mg) was added to a solution of N-[2-(1-t-butoxycarbonylpiperidin-4-yl)phenyl]methanesulfonamide (650 mg) in tetrahydrofuran (50 mL) and the mixture was stirred at room temperature for 1 h. Methyl iodide (260 mg) was added and the mixture was stirred at room temperature for 36 h. The solvent was evaporated under reduced pressure, and the residue was partitioned between water 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 colorless solid (662 mg), δH (CDCl3) 1.48 (9H, s), 1.73 (2H, m), 1.88 (2H, m), 2.84 (2H, m), 2.97 (3H, s), 3.25 (3H, s), 3.33 (1H, m), 4.13 (2H, m), 7.21-7.36 (4H, m). m/e (ES+) 369 (MH+).

Workup

  1. stirringthe mixture was stirred at room temperature for 36 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf83b2e14f674cb5b6f89c391c441c76
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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