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

HRID 1895705Notes

Reaction equation

HRID 1895705 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].C(N(CC)CC)C.[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 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(5-propylpyrimidin-2-yl)piperidin-4-ol (16.1 g, 72.8 mmol) and triethylamine (10.14 mL, 72.8 mmol) in CH2Cl2 (150 mL) at 0° C. was added methanesulfonyl chloride (4.76 mL, 80 mmol) slowly. After stirring at rt for 1.5 h, the mixture was quenched with 15 ml water followed by 15 ml 1N HCl. The organic layer was collected and the aqueous layer was extracted with CH2Cl2. The combined organic layers were then washed with saturated aqueous NaHCO3 and brine. After drying over Na2SO4, the organic layer was concentrated to give the desired product 1-(5-propylpyrimidin-2-yl)piperidin-4-yl methanesulfonate (21 g, 70.1 mmol, 96% yield) as yellow solid. MS (ESI) 300.2 (M+1).

Workup

  1. customthe mixture was quenched with 15 ml water
  2. customThe organic layer was collected
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were then washed with saturated aqueous NaHCO3 and brine
  5. dry with materialAfter drying over Na2SO4
  6. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-e132751d3f8b4ce0a837c40c248e6453
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

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