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

HRID 489644Notes

Reaction equation

HRID 489644 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.N1C=CC=CC=1.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCCl>[CH3:27][S:28]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]1)(=[O:30])=[O:29]

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 82.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 100 mL round-bottomed flask was added tert-butyl 4-(2-aminophenyl)piperidinecarboxylate (Preparation B) (1.93 g, 7.2 mmol) and 1,2-dichloroethane (50 mL). The solution was magnetically stirred under a N2 atmosphere, treated with pyridine (2.9 mL, 36 mmol) and methanesulfonyl chloride (Aldrich) (1.1 mL, 1.7 g, 14 mmol). The vessel was immersed in a 50° C. oil bath for 6 h then cooled to 25° C. The solvent was removed in vacuo, and the residue was partitioned between EtOAc (200 mL) and 1 N HCl (100 mL). The organic layer was washed with satd NaHCO3 (75 mL), satd NaCl (50 mL), dried over Na2SO4, filtered and concentrated to give a foam. The foam was purified by silica gel chromatography (3:/EtOAc:hexane) to provide the title compound as a white foam (2.1 g). MS (ESI, pos. ion) m/z: 355 (M+1); (ESI, neg. ion) m/z: 353 (M−1). Calc'd for C17H26N2O4S: 354.47.

Workup

  1. customwas immersed in a 50° C.
  2. customfor 6 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between EtOAc (200 mL) and 1 N HCl (100 mL)
  5. washThe organic layer was washed with satd NaHCO3 (75 mL), satd NaCl (50 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a foam
  10. customThe foam was purified by silica gel chromatography (3:/EtOAc:hexane)

Sources & evidence

ORD record
ord-63ecb60233a941ce84226f6a9cc5f46f
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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