Triethylamine → 1-Methanesulfonyl-piperidine-4-carboxylic acid benzyl ester

HRID 1037744Notes

Reaction equation

HRID 1037744 reaction equation
Cl.[CH2:2]([O:9][C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CN(C=O)C.O>[CH2:2]([O:9][C:10]([CH:12]1[CH2:17][CH2:16][N:15]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:14][CH2:13]1)=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68664822Benzyl piperidine-4-carboxylate hydrochloride

Product 1

HCID 574280631-Methanesulfonyl-piperidine-4-carboxylic acid benzyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Piperidine-4-carboxylic acid benzyl ester, hydrochloride salt (1 g, 3.9 mmol, 1 e.) from step 3, was dissolved in DMF (15 ml), Triethylamine (0.55 ml, 4 mmol, 1 eq.) and methanesulfonylchloride were added. The mixture was stirred for 1 h at room temperature, then was poured in water (20 ml). The aqueous solution was extracted with Ethyl Acetate (90 ml) and the organic layer was dried over anhydrous sodium sulfate, evaporated under reduced pressure to give a colourless oil. Yield 78%, 0.9 g.

Workup

  1. extractionThe aqueous solution was extracted with Ethyl Acetate (90 ml)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated under reduced pressure
  4. customto give a colourless oil

Sources & evidence

ORD record
ord-a24d30d42e5544f5bc1ebe59baffe661
Source dataset
uspto-grants-2013_10
Patent number
US08546608B2

Reaction notes

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