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

HRID 400760Notes

Reaction equation

HRID 400760 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, 0.099 mol) in dimethyl sulfoxide (230 mL) and water (70 mL), were added 2-ethylpiperidine (14.4 mL, 0.1083 mol) and sodium carbonate (20.88 g, 0.197 mol). The resulting mixture was heated at 110° C. for a period of 30 h. The reaction mixture was cooled to room temperature, diluted with water (1000 mL), extracted by methyl tert-butyl ether (2×500 mL), dried using sodium sulphate and concentrated under reduced pressure. The resulting crude was purified by column chromatography on silica gel (60-120 mesh) using pet ether as eluent to afford the titled compound as a yellow liquid. 1H NMR (DMSO-d6, 400 MHz) δ 10.15 (1H, s), 7.70-7.73 (2H, d), 7.22-7.25 (1H, m), 3.08-3.13 (2H, m), 2.84-2.86 (1H, m), 1.83-1.84 (1H, m), 1.34-1.67 (7H, m), 0.62-0.66 (3H, t).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted by methyl tert-butyl ether (2×500 mL)
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude was purified by column chromatography on silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-0144d99219824faa975829465bfd7273
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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