Triethylamine → HCID 22678470, compound

HRID 1837699Notes

Reaction equation

HRID 1837699 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH2:16][CH2:17][OH:18])=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]2[CH2:16][CH:17]=[O:18])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22678507HCID 22678507, compound

Product 1

HCID 22678470HCID 22678470, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 4.2 g of pyridine-sulfurtrioxide complex dissolved in dimethyl sulfoxide (DMSO) was added dropwise into a solution of 3 g of 2-[1-[(2-methoxy-3-pyridyl)methyl]-2-piperidyl]-1-ethanol and 7.3 ml of triethylamine dissolved in 15 ml of DMSO, while keeping the bulk temperature at 20° C. or less. After completing the dropwise addition, the mixture was stirred at room temperature for one hour. An aqueous sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. After drying over sodium sulfate, the solvent was evaporated. The residue was purified by silica gel chromatography (methanol), to give 2.5 g of a red brown oil.

Workup

  1. customat 20° C. or less
  2. additionthe dropwise addition
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel chromatography (methanol)

Sources & evidence

ORD record
ord-b79731c3b7044f689eba7de70e88e2ef
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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