4-Toluenesulfonyl chloride → HCID 54315052, compound

HRID 1530521Notes

Reaction equation

HRID 1530521 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][OH:9].[H-].[Na+].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]>CN(C=O)C>[CH3:19][C:18]1[CH:20]=[CH:21][C:15]([S:12]([O:9][CH2:8][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][N:2]2[CH3:1])(=[O:14])=[O:13])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 893941-Methyl-2-piperidinemethanol

Product 1

HCID 54315052HCID 54315052, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of (1-methylpiperidin-2-yl)methanol (1.00 g, 7.75 mmol) in dry DMF (5.0 mL) at 0° C. was added NaH (620 mg, 15.5 mmol, 60% in mineral oil). After being stirred for 1 h, TsCl (2.96 g, 15.5 mmol) in DMF (1.0 mL) was added. The resulting mixture was further stirred at room temperature for 10 h and then poured into the ice-water (20 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The organic layers were dried over Na2SO4 and evaporated to dryness to afford the crude product, which was purified by silica gel chromatography eluting with a 20% gradient of EtOAc in petroleum ether to afford (1-methylpiperidin-2-yl)methyl 4-methylbenzenesulfonate (800 mg, 36.5% yield). LCMS (ESI) m/z: 284.2 [M+H+]

Workup

  1. stirringThe resulting mixture was further stirred at room temperature for 10 h
  2. extractionThe resulting mixture was extracted with EtOAc (2×50 mL)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. customevaporated to dryness
  5. customto afford the crude product, which
  6. customwas purified by silica gel chromatography
  7. washeluting with a 20% gradient of EtOAc in petroleum ether

Sources & evidence

ORD record
ord-865fb753aa26475dbda2808b7140a536
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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