Methanol → 1-(Pyridin-2-yl)piperidin-4-ol

HRID 517948Notes

Reaction equation

HRID 517948 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])C.[CH3:15][OH:16]>>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:10]1[CH2:11][CH2:12][CH:15]([OH:16])[CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 887MethanolHCID 8471TriethylamineHCID 97462-Fluoropyridine

Product 1

HCID 106074171-(Pyridin-2-yl)piperidin-4-olYield 64.7%

Procedure

1-(pyridin-2-yl)piperidin-4-ol (64.7% yield), 2-fluoropyridine (29.7 mmol, 2.88 g) and triethylamine (49.4 mmol, 6.89 ml, 5.00 g) were dissolved in MeOH (2.5 ml) and heated to 150° C. for 1 hour in the microwave. The solvent was removed at reduced pressure. The resulting residue was purified by column chromatography, eluting with DCM—3% MeOH/DCM to afford 1-(pyridin-2-yl)piperidin-4-ol. (1.14 g) 1H NMR (CDCl3) δ: 8.18 (d, 1H), 7.45 (m, 1H), 6.67 (d, 1H), 6.58 (m, 1H), 4.06 (m, 2H), 3.92 (br, 1H), 3.15 (m, 2H), 1.98 (m, 2H), 1.59 (m, 2H).

Sources & evidence

ORD record
ord-b4594037cb7f40f0aba9e5095add9c2d
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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