Triethylamine → 5-Propylpyrimidin-2-ylpiperidin-4-yl methanesulfonate

HRID 1518468Notes

Reaction equation

HRID 1518468 reaction equation
[CH2:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)=[N:8][CH:9]=1)[CH2:2][CH3:3].CCN(CC)CC.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(Cl)Cl>[CH3:24][S:25]([O:16][CH:13]1[CH2:14][CH2:15][N:10]([C:7]2[N:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][N:6]=2)[CH2:11][CH2:12]1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 670724781-(5-Propylpyrimidin-2-yl)piperidin-4-ol

Product 1

HCID 866262675-Propylpyrimidin-2-ylpiperidin-4-yl methanesulfonateYield 558.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 1-(5-propylpyrimidin-2-yl)piperidin-4-ol (9.2 g, 41.6 mmol), Et3N (12.85 mL, 91 mmol, Aldrich) in CH2Cl2 (80 mL) at 0° C. was added a solution of Methanesulfonyl chloride (3.54 mL, 45 7 mmol, Acros) in CH2Cl2 (20 mL) dropwise. The reaction mixture was stirred at room temperature for 1 h and washed with 1N HCl in H2O, saturated NaHCO3 in H2O and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to yield 11.7 g of the desired product as an off-white solid. MS (ESI) 300 (M+H).

Workup

  1. washwashed with 1N HCl in H2O, saturated NaHCO3 in H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-768cb1ce02164018b2309200d16b2605
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

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