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

HRID 1445800Notes

Reaction equation

HRID 1445800 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]([CH3:26])=[C:17]([CH2:19][CH2:20]OS(C)(=O)=O)[N:18]=2)=[CH:10][CH:9]=1>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:15][C:16]([CH3:26])=[C:17]([CH2:19][CH2:20][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:18]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester2×

Product 1

HCID 116602921-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-piperidineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add piperidine (3.04 g, 36.11 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. Purify crude on silica gel, eluting with 5% 2N NH3 in methanol/dichloromethane to give 1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-piperidine (0.944 g, 75%).

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
  9. customPurify crude on silica gel
  10. washeluting with 5% 2N NH3 in methanol/dichloromethane

Sources & evidence

ORD record
ord-f652b49cbe074d5481bbce345efb6a44
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

Loading…