Sodium Carbonate → 5-Bromo-2-(2-ethylpiperidin-1-YL)benzaldehyde

HRID 2410488Notes

Reaction equation

HRID 2410488 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]1)[CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:13]2[CH2:11][CH3:12])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 942052-EthylpiperidineHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 585541245-Bromo-2-(2-ethylpiperidin-1-YL)benzaldehyde

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (20 g, 99 mmol) in DMSO (230 mL) and water (70 mL) were added 2-ethylpiperidine (14.4 mL, 108 mmol) and sodium carbonate (20.9 g, 197 mmol). The resulting mixture was heated at 110° C. for 30 hours. The reaction mixture was cooled at RT, diluted with water (1000 mL) and extracted with MTBE (2×500 mL). The organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure. After purification by flash chromatography (silica, pet ether), the title compound was obtained as a yellow oil. 1H NMR (DMSO-d6, 400 MHz) δ 10.15 (1H, s), 7.72 (2H, d), 7.24 (1H, m), 3.11 (2H, m), 2.85 (1H, m), 1.84 (1H, m), 1.34-1.67 (7H, m), 0.64 (3H, t).

Workup

  1. temperatureThe reaction mixture was cooled at RT
  2. extractionextracted with MTBE (2×500 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customAfter purification by flash chromatography (silica, pet ether)

Sources & evidence

ORD record
ord-ad72edb511014c6e88646de19de26a0c
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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