Triethylamine → Ethyl 1-(methylsulfonyl)piperidine-4-carboxylate

HRID 429818Notes

Reaction equation

HRID 429818 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][C:9]([CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:10])[CH3:7].C(N(CC)CC)C>ClCCl>[CH2:6]([O:8][C:9]([CH:11]1[CH2:16][CH2:15][N:14]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:13][CH2:12]1)=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 669104Ethyl 1-(methylsulfonyl)piperidine-4-carboxylateYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A solution of methanesulfonyl chloride (28 ml, 0.36 mole) in dichloromethane (50 ml) was added dropwise to a solution of piperidine-4-carboxylic acid ethyl ester (50 grams, 0.32 mole) and triethylamine (53 ml, 0.38 mole) in dichloromethane (350 ml) at 0° C. The reaction mixture was stirred at 0-5° C. for 3 hours. The solution was washed with 2×100 ml water, dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The solid residue was triturated with 100 ml ethyl ether, collected by filtration and dried to give 1-methanesulfonylpiperidine-4-carboxylic acid ethyl ester (68 grams, 90%), m.p. 91-92° C.

Workup

  1. washThe solution was washed with 2×100 ml water
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe solid residue was triturated with 100 ml ethyl ether
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c4c499e0b7464f73b89fc56668ada4cc
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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