Pyridine → HCID 70192656, compound

HRID 1419577Notes

Reaction equation

HRID 1419577 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.N1C=CC=CC=1>ClCCl.CN(C)C1C=CN=CC=1>[C:23]([O:22][C:20]([N:17]1[CH2:16][CH2:15][CH:14]([CH2:13][N:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:2]([CH3:1])(=[O:4])=[O:3])[CH2:19][CH2:18]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 54356602HCID 54356602, compound

Product 1

HCID 70192656HCID 70192656, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.77 mL, 1.13 g, 9.9 mmol) was added dropwise to a stirred, cooled (0° C.) solution of N-phenyl-1-t-butoxycarbonylpiperidine-4-methylamine (2.61 g, 9 mmol) and pyridine (1.09 mL, 1.07 g, 13.5 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 16 h. The mixture was cooled in ice and 4-dimethylaminopyridine (220 mg, 1.8 mmol), pyridine (1.09 mL, 1.07 g, 13.5 mmol) and methanesulfonyl chloride (0.77 mL, 1.13 g, 9.9 mmol) were added. The mixture was stirred at room temperature for 24 h. The solvent was evaporated under reduced pressure, aqueous sodium hydrogen carbonate (saturated, 50 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic fractions were washed with aqueous citric acid (10%, 2×50 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane (2:1, 30 mL) to give the title compound as a colorless solid (2.96 g, 89%), δH (250 MHz, CDCl3) 7.46-7.31 (5H, m), 4.06 (2H, m), 3.56 (2H, d, J 7.2 Hz), 2.85 (3H, s), 2.60 (2H, m), 1.71 (2H, m), 1.57 (1H, m), 1.43 (9H, s), and 1.05 (2H, m).

Workup

  1. temperatureThe mixture was cooled in ice
  2. stirringThe mixture was stirred at room temperature for 24 h
  3. customThe solvent was evaporated under reduced pressure, aqueous sodium hydrogen carbonate (saturated, 50 mL)
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  6. washThe combined organic fractions were washed with aqueous citric acid (10%, 2×50 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate/hexane (2:1, 30 mL)

Sources & evidence

ORD record
ord-50f0a5598cd6462eaf42856c5052022f
Source dataset
uspto-grants-1999_03
Patent number
US05885999

Reaction notes

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