Methyl Ethyl Ketone → HCID 18174717, compound

HRID 395608Notes

Reaction equation

HRID 395608 reaction equation
Cl[C:2]1[O:3][C:4]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[NH:26]1[CH2:36][CH2:35][CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:27]1.CC(=O)CC>C(OCC)(=O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([N:26]3[CH2:27][CH2:28][CH:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:35][CH2:36]3)[O:3][C:4]=2[CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 70770Ethyl 4-piperidinecarboxylateHCID 109598002-Chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole

Product 1

HCID 18174717HCID 18174717, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole (378 mg), ethyl isonipecotate (1.57 g) and 2-butanone (10 ml) was stirred with heating under reflux for 6 hours. The reaction mixture was diluted with ethyl acetate (100 ml), and the organic layer was washed with a 10% aqueous solution of citric acid (50 ml) and dried over anhydrous magnesium sulfate. After the organic layer was concentrated, the residue was recrystallized from ethyl acetate-hexane to give ethyl N-[4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]-2-oxazolyl]isonipecotate as pale yellow prisms (345 mg, 69%). Melting point 80-81° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 6 hours
  3. washthe organic layer was washed with a 10% aqueous solution of citric acid (50 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter the organic layer was concentrated
  6. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-967c858ccb8248c39fa2668d00756db7
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Reaction notes

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