Triethylamine → (1-(4-Methylpyridin-2-yl)piperidin-4-yl)methanol

HRID 517953Notes

Reaction equation

HRID 517953 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.F[C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=1.C(N(CC)CC)C>>[CH3:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)[CH:15]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 4207714-PiperidinemethanolHCID 27374032-Fluoro-4-methylpyridine

Product 1

HCID 61725157(1-(4-Methylpyridin-2-yl)piperidin-4-yl)methanol

Conditions

Temperature
150 °C

Procedure

Piperidin-4-ylmethanol (8.68 mmol, 1 g), 2-fluoro-4-methylpyridine (26.0 mmol, 2.89 g) and triethylamine (26.0 mmol, 3.63 mL, 2.64 g) were combined and heated to 150° C. for 1 hour in the microwave. The solvent was removed at reduced pressure and the residue purified by silica chromatography eluting with DCM—2% MeOH/CM to afford (1-(4-methylpyridin-2-yl)piperidin-4-yl)methanol. (0.75 g) MS m/z 207.2 (M+H).

Workup

  1. customThe solvent was removed at reduced pressure
  2. customthe residue purified by silica chromatography
  3. washeluting with DCM—2% MeOH/CM

Sources & evidence

ORD record
ord-5921f6bc04f0408e8ceff60b6a6498e4
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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