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

HRID 1445836Notes

Reaction equation

HRID 1445836 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 100.9%

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, 3.6 mmol) in anhydrous THF (15 mL). Heat the reaction mixture at reflux overnight and cool to room temperature. Wash the organic material with 1N HCl (50 mL) and extract the aqueous layer with diethyl ether (2×50 mL). Add SN NaOH to the aqueous layer (pH >10) and extract with dichoromethane (2×50 mL). Dry the organic extracts over Na2SO4, filter and concentrate to give 1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-2-methylpiperidine (1.32 g, quantitative).

Workup

  1. temperatureHeat the reaction mixture
  2. temperatureat reflux overnight
  3. washWash the organic material with 1N HCl (50 mL)
  4. extractionextract the aqueous layer with diethyl ether (2×50 mL)
  5. extractionAdd SN NaOH to the aqueous layer (pH >10) and extract with dichoromethane (2×50 mL)
  6. dry with materialDry the organic extracts over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-b1b7a2a8e9f94f7e86e52fd1c647da0e
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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