Triethylamine → 2-(N-methanesulfonyl-4-piperidinyloxy)-5-chloropyridine

HRID 1582064Notes

Reaction equation

HRID 1582064 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]=2)[CH2:3][CH2:2]1.CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([N:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][N:9]=2)[CH2:3][CH2:2]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 112643295-Chloro-2-(piperidin-4-yloxy)pyridine

Product 1

HCID 227197192-(N-methanesulfonyl-4-piperidinyloxy)-5-chloropyridineYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution 2-(4-piperidinyloxy)-5-chloropyridine(12.9 g, 0.06 mol) and Et3N (25.4 ml, 0.182 mol) in dry dichloromethane (400 ml) at 0° C. and under Argon, was added methanesulfonyl chloride (5.3 ml, 0.067 mol) in dry dichloromethane (100 ml), dropwise. The mixture was stirred for 20 hours at room temperature. The mixture was diluted with dichloromethane (250 ml), then washed with water (×3) then brine. The organic layers were dried with Na2SO4 and evaporated in vacuo. The residue was triturated and washed with diethylether to give 2-(N-methanesulfonyl-4-piperidinyloxy)-5-chloropyridine (15.1 g) as a pale yellow solid.

Workup

  1. washwashed with water (×3)
  2. dry with materialThe organic layers were dried with Na2SO4
  3. customevaporated in vacuo
  4. customThe residue was triturated
  5. washwashed with diethylether

Sources & evidence

ORD record
ord-97ee7243a24d4f11b155705a57c6c212
Source dataset
uspto-grants-2004_05
Patent number
US06734184B1

Reaction notes

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