Methanesulfonyl chloride → HCID 23133422, compound

HRID 1008768Notes

Reaction equation

HRID 1008768 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>ClCCl.O>[CH3:17][S:18]([N:12]1[CH2:11][CH2:10][N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][N:7]=2)[CH2:14][CH2:13]1)(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 6676181-(5-Trifluoromethyl-pyridin-2-yl)-piperazine

Product 1

HCID 23133422HCID 23133422, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-(trifluoromethyl)pyridin-2-yl]piperazine (23 g, 0.099 mol) and TEA (42 mL 0.298 mol) in dry dichloromethane (400 mL) maintained at 0° C. under nitrogen atmosphere, was added methanesulfonylchloride (12.6 g, 0.109 mol) over a period of 20 min. The reaction mixture was stirred at room temperature for 6 h and diluted with water. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtrated and concentrated. The crude product was recrystallized from petrol ether:EtOAc (9:1) to afford the title compound as a solid (27 g, 87% yield). TLC: Rf=0.75 (Chloroform:MeOH; 9:1). 1H NMR (CDCl3, 300 MHz) δ: 2.82 (3H, s), 3.32 (4H, m), 3.79 (4H, m), 6.68) (1H, d, J=9 Hz), 7.68 (1H, d, J=9 Hz), 8.42 (1H, s).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. customThe crude product was recrystallized from petrol ether:EtOAc (9:1)

Sources & evidence

ORD record
ord-f1ce0260617846cba35223da7ec29b2f
Source dataset
uspto-grants-2011_07
Patent number
US07973039B2

Reaction notes

Loading…