Triethylamine → (1-(4-Methylpyridin-2-yl)piperidin-4-yl)methyl methanesulfonate

HRID 517954Notes

Reaction equation

HRID 517954 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]2)[CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:15][CH2:14][CH:11]1[CH2:12][CH2:13][N:8]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=2)[CH2:9][CH2:10]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 61725157(1-(4-Methylpyridin-2-yl)piperidin-4-yl)methanol

Product 1

HCID 86673349(1-(4-Methylpyridin-2-yl)piperidin-4-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-(4-Methylpyridin-2-yl)piperidin-4-yl)methanol (0.970 mmol, 0.2 g) and triethylamine (2.91 mmol, 0.404 mL, 0.294 g) were stirred in DCM at 0° C. Methanesulfonyl chloride (1.454 mmol, 0.113 mL, 0.167 g) was added dropwise and the reaction allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was washed with water, dried over Na2SO4 and concentrated in vacuo to afford (1-(4-methylpyridin-2-yl)piperidin-4-yl)methyl methanesulfonate. (0.234 g)

Workup

  1. washThe reaction mixture was washed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf002950ef5f45cfb2ee204857de9227
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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