Triethylamine → HCID 19772597, compound

HRID 344685Notes

Reaction equation

HRID 344685 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].O[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][C:12]([C:26]([O:28][CH3:29])=[O:27])([N:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16](=[O:19])[CH2:17][CH3:18])[CH2:11][CH2:10]1.C(N(CC)CC)C>C(OCC)(=O)C>[CH3:1][S:2]([CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][C:12]([C:26]([O:28][CH3:29])=[O:27])([N:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16](=[O:19])[CH2:17][CH3:18])[CH2:13][CH2:14]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19772580HCID 19772580, compound

Product 1

HCID 19772597HCID 19772597, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methanesulfonyl chloride 0.374 g, 3.3 mmol in ethyl acetate (3ml was added to a mixture of 1-(2-hydroxyethyl)-4-methoxycarbonyl-4-(N'-phenylpropionamido) piperidine (1.0 g, 3 mmol) and triethylamine. The resulting mixture was stirred overnight. The reaction mixture was filtered and the filtrate was concentrated under vacuum to give an oily residue. The residue was chromatographed on silica gel (290 g; ethyl acetate/hexane: 1:4) to yield 1-(2-methanesulfonylethyl)-4-methoxycarbonyl-4-(N'-phenyl-propionamido)piperidine (0.53 g, 43%) as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto give an oily residue
  4. customThe residue was chromatographed on silica gel (290 g; ethyl acetate/hexane: 1:4)

Sources & evidence

ORD record
ord-07bdc489d26b42d398fd99aa2dcc9e70
Source dataset
uspto-grants-1991_10
Patent number
US05053411

Reaction notes

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