Triethylamine → 1-(4-Methyl-2-pyridinyl)-4-(methylsulfonyl)piperazine

HRID 1775344Notes

Reaction equation

HRID 1775344 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:10][CH2:9]2)[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 27600581-(4-Methylpyridin-2-yl)piperazine

Product 1

HCID 898260101-(4-Methyl-2-pyridinyl)-4-(methylsulfonyl)piperazineYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 1-(4-methyl-2-pyridyl)piperazine (228 mg, 1.286 mmol) in DCM (10 ml) were added triethylamine (360 μl, 2.59 mmol) and methanesulfonyl chloride (105 μl, 2.59 mmol). The mixture was stirred at 0° C. for one hour, then a saturated solution of sodium bicarbonate was added, the layers were separated, the aqueous layer was extracted with DCM (2×), the organic layers were combined, dried (sodium sulfate) and concentrated under reduced pressure to yield 316 mg of a white solid (1.238 mmol, yield 96%) MS (ESI) m/z=256.1 [M+1]+.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with DCM (2×)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-20af93d2e879493286abf166b7a243bb
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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