Potassium Carbonate → 1-(5-Bromopyridin-2-yl)piperidin-4-ol

HRID 2383582Notes

Reaction equation

HRID 2383582 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[OH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:13]2[CH2:14][CH2:15][CH:10]([OH:9])[CH2:11][CH2:12]2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 79341Piperidin-4-ol

Product 1

HCID 218978371-(5-Bromopyridin-2-yl)piperidin-4-olYield 493.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,5-dibromopyridine (100 mg, 0.42 mmol), 4-hydroxypiperidine (49 mg, 0.46 mmol) and K2CO3 (64 mg, 0.46 mmol) in ethanol (4 mL) was heated to 110° C. for 52 h. The crude reaction mixture was concentrated under reduced pressure to dryness and the residue was treated with water. Crude product was collected by vacuum filtration and purified by flash chromatography using EtOAc/hexanes (1:4 to 2:3) to give the title compound as a white solid (533 mg, 41%). 1H NMR (400 MHz, CDCl3) δ 8.18 (d, J=2.2 Hz, 1H), 7.53 (dd, J=9.0, 2.3 Hz, 1H), 6.59 (d, J=9.0 Hz, 1H), 4.04-3.94 (m, 3H), 3.18 (t, J=11 Hz, 2H), 2.00-1.95 (m, 2H), 1.63-1.54 (m, 2H); MS ESI 256.9 [M+H]+, calcd for [C10H13BrN2O+H]+ 257.02.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure to dryness
  3. additionthe residue was treated with water
  4. filtrationCrude product was collected by vacuum filtration
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-4d6f623601804579800c8652e3071262
Source dataset
uspto-grants-2012_09
Patent number
US08263596B2

Reaction notes

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