N-Methylpiperidine → 24192-95-8

HRID 601006Notes

Reaction equation

HRID 601006 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.C[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCOCC1>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[N:7]=1

Participants

4

Reactant 2

HCID 12291N-MethylpiperidineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 81734624192-95-8Yield 12%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

These intermediates were prepared following a procedure by K. Yoshida et al, J. Chem. Soc. Perkins Transactions I., (1992), 919-922. A solution of 2,4-dichloropyrimidine (4.00 g, 26.8 mmol) and 1-methyl-piperidine (3.25 mL, 29.5 mmol) in 1,4-dioxane (60 mL) was stirred at 100° C. for 3 d, then cooled and evaporated. Purification by flash chromatography (SiO2) eluted with 15:85 ethyl acetate: hexanes provided 4-chloro-2-piperidin-1-yl-pyrimidine (0.58 g, 12% yield) as a pale yellow solid: 1H-NMR (CDCl3, 500 MHz) 8.06 (d, 1H), 6.37 (d, 1H), 3.70 (m, 4H), 1.61 (m, 2H), 1.53 (m, 4H) ppm; MS (FIA) 198.1 (M+H); HPLC (method A) 3.550 min. and 2-chloro-4-piperidin-1-yl-pyrimidine (1.87 g, 38% yield) as a white solid: 1H-NMR (CDCl3, 500 MHz) 8.01 (d, 1H), 6.41 (d, 1H), 3.65 (m, 4H), 1.73 (m, 2H), 1.65 (m, 4H) ppm; MS (FIA) 198 (M+H); HPLC (method A) 2.583 min.

Workup

  1. customThese intermediates were prepared
  2. temperaturecooled
  3. customevaporated
  4. customPurification by flash chromatography (SiO2)
  5. washeluted with 15:85 ethyl acetate

Sources & evidence

ORD record
ord-cc1302f803c946a8a42e0764b100fc3b
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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