Triethylamine → Methanesulfonic acid 1-methoxy-piperidin-4-yl ester

HRID 2035306Notes

Reaction equation

HRID 2035306 reaction equation
[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>C(OCC)(=O)C>[CH3:1][O:2][N:3]1[CH2:8][CH2:7][CH:6]([O:9][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 30226061-Methoxypiperidin-4-ol

Product 1

HCID 86663299Methanesulfonic acid 1-methoxy-piperidin-4-yl esterYield 126.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

21 g 1-Methoxy-piperidin-4-ol (from Step 1) and 19.4 g triethylamine were dissolved in 200 ml ethyl acetate, and cooled to 0° C. 15.0 g Methanesulfonyl chloride was added slowly. The resulting white suspension was stirred at 0° C. for 1 hour, then at room temperature for an additional 1 hour. Then the mixture was filtered and the solvent evaporated, yielding 34.6 g of methanesulfonic acid 1-methoxy-piperidin-4-yl ester. This material was used for the next step without further purification.

Workup

  1. waitat room temperature for an additional 1 hour
  2. filtrationThen the mixture was filtered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-a4235c195d2e4a28a2782dc713e599bd
Source dataset
uspto-grants-2013_11
Patent number
US08574607B2

Reaction notes

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