4-Toluenesulfonyl chloride → (1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

HRID 2371139Notes

Reaction equation

HRID 2371139 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:15][CH2:14][CH:10]2[CH2:11][CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10398044(1-Benzylpiperidin-3-yl)methanol

Product 1

HCID 57656889(1-Benzylpiperidin-3-yl)methyl 4-methylbenzenesulfonateYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-benzylpiperidin-3-yl)methanol (820 mg) and triethylamine (0.84 mL) in dichloromethane (10 mL) was added para-toluenesulfonyl chloride (846 mg). The solution was stirred overnight at room temperature. The mixture was partitioned between dichloromethane and water. The layers were separated and the organic layer was dried over sodium sulfate and evaporated. The residue was purified by silica column chromatography, eluting with a gradient of 0 to 50% ethyl acetate in hexane to give the title compound as a colourless oil (1.15 g, 80%).

Workup

  1. customThe mixture was partitioned between dichloromethane and water
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica column chromatography
  6. washeluting with a gradient of 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-05c245cf1ca34feb8201bc21e8b20d0f
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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