Triethylamine → 1-Methylpiperidin-4-yl methanesulfonate

HRID 1052259Notes

Reaction equation

HRID 1052259 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 660484-Piperidinol, 1-methyl-

Product 1

HCID 41906811-Methylpiperidin-4-yl methanesulfonateYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxy-N-methylpiperidine (200 μL, 1.70 mmol) was dissolved in methylene chloride (10 mL) and then cooled to 0° C. Triethylamine (296 μL, 2.13 mmol) was added, followed by the addition of methanesulfonyl chloride (145 μL, 1.87 mmol). After 1.5 hours, the reaction was quenched with water, and extracted with methylene chloride. The combined organic layers were dried over MgSO4, then concentrated under vacuum to give the desired product (280 mg, 88%). LCMS calculated for C7H16NO3S (M+H)+: m/z=194.1. Found: 194.1.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-cb8960c1db4f47ae88ee124eaa3288b1
Source dataset
uspto-grants-2016_07
Patent number
US09388185B2

Reaction notes

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