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

HRID 1445828Notes

Reaction equation

HRID 1445828 reaction equation
C[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.ClCCl>O1CCCC1>[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[CH2:2][CH2:7][CH2:6][CH2:5][CH2:4]3)[N:19]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 79742-MethylpiperidineHCID 11451238Methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester

Product 1

HCID 116602921-{2-[2-(4-Bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-piperidineYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Add 2-methyl piperidine (0.871 g, 8.77 mmol) to a solution of methanesulfonic acid 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl ester (0.316 g, 0.877 mmol) in tetrahydrofuran (5 mL) in a sealed tube, and heat at 60° C. overnight. Cool to room temperature and add dichloromethane. Wash the crude organic material with saturated sodium chloride solution. Dry the organic layer over Na2SO4, filter, and concentrate. Purify on silica gel eluting with 10% ammoniated methanol in dichloromethane to give (+/−)-1-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethyl}-piperidine (0.215 g, 67%): MS (m/e): 363 (M+1).

Workup

  1. temperatureCool to room temperature
  2. washWash the crude organic material with saturated sodium chloride solution
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify on silica gel eluting with 10% ammoniated methanol in dichloromethane

Sources & evidence

ORD record
ord-c02762584dfd40a5b23fb78f27ca3e41
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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