2-Methylpiperidine → 1-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine

HRID 1445816Notes

Reaction equation

HRID 1445816 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]([CH3:27])=[C:18]([CH2:20][CH2:21]OS(C)(=O)=O)[N:19]=2)=[CH:11][CH:10]=1>C1COCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[O:16][C:17]([CH3:27])=[C:18]([CH2:20][CH2:21][N:3]3[CH2:4][CH2:5][CH2:6][CH2:7][CH:2]3[CH3:1])[N:19]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 79742-MethylpiperidineHCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester2×

Product 1

HCID 115160701-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidineYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 2-methylpiperidine (3.55 g, 36.1 mmol) to a solution of Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester (See Intermediate 13) (1.3 g, 3.61 mmol) in anhydrous THF (15 mL). Reflux the reaction overnight and cool. Wash organic material with 1N HCl (50 mL) and extract aqueous layer with diethyl ether (2×50 mL). Add 5N NaOH to aqueous layer (pH>10) and extract with dichoromethane (2×50 mL). Dry organics over Na2SO4, filter and concentrate to give 1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine (1.32 g, quant).

Workup

  1. temperatureReflux
  2. customthe reaction overnight
  3. temperaturecool
  4. extractionWash organic material with 1N HCl (50 mL) and extract aqueous layer with diethyl ether (2×50 mL)
  5. additionAdd 5N NaOH to aqueous layer (pH>10)
  6. extractionextract with dichoromethane (2×50 mL)
  7. filtrationDry organics over Na2SO4, filter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-2d731806d2624eb8b26929e65b9715c7
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…