Triethylamine → HCID 23503188, compound

HRID 1909706Notes

Reaction equation

HRID 1909706 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].C(N(CC)CC)C.[S:16](Cl)(Cl)(=[O:18])=[O:17]>ClCCl>[S:16]1(=[O:18])(=[O:17])[N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[CH2:7][O:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 94263Piperidin-2-ylmethanol

Product 1

HCID 23503188HCID 23503188, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a −78° C. hazy solution under a nitrogen atmosphere of racemic 2-piperidinemethanol (0.576 g, 5.00 mmol) and triethylamine (1.42 mL, 10.0 mmol) in anhydrous dichloromethane (30 mL) was added a solution of sulfuryl chloride (0.41 mL, 5.06 mmol) in anhydrous dichloromethane (30 mL) and the reaction was stirred for around 18 h from −78° C. to ambient temperature. The clear, yellow solution was washed with 1.0N HCl (2×25 mL) and brine (25 mL), dried over Na2SO4, concentrated in vacuo to a dark yellow oil, and purified by flash column chromatography (silica gel, ether) to afford the title product as a clear yellow oil (0.342 g, 39%). The proton NMR was identical to the desired product in procedure A, step 2.

Workup

  1. washThe clear, yellow solution was washed with 1.0N HCl (2×25 mL) and brine (25 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo to a dark yellow oil
  4. custompurified by flash column chromatography (silica gel, ether)

Sources & evidence

ORD record
ord-1ce3c84f2dd24da99b58be963019645c
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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