Ammonium Acetate → 1-(3-Benzyloxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine

HRID 1741395Notes

Reaction equation

HRID 1741395 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:38]=[CH:39][CH:40]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[C:20]([O:22][CH:23]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:45]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:38]=[CH:39][CH:40]=1)[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[C:20]1[O:22][C:23]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:45]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 542478562-Oxo-1,2-diphenylethyl 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylate

Product 1

HCID 183673361-(3-Benzyloxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidineYield 37.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-oxo-1,2-diphenylethyl 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylate (288 mg) and ammonium acetate (427 mg) in acetic acid (1.4 ml) was stirred under reflux for 3 hours, cooled to room temperature, and partitioned between ethyl acetate and aqueous NaHCO3. The organic layer was washed with aqueous NaHCO3 (twice) and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 1-(3-benzyloxybenzoyl)-2-(4,5-diphenyl-2-oxazolyl)piperidine (104 mg) as amorphous powder. (+) APCI-MS (m/z): 515 (M+ +1) IR (Nujol): 1630 cm-1NMR (CDCl3, δ): 1.45-2.05 (6H, m), 2.4-3.75 (2H, m), 4.7-5.25 (3H, m), 7.01-7.37 (15H, m), 7.57-7.67 (4H, m)

Workup

  1. temperatureunder reflux for 3 hours
  2. custompartitioned between ethyl acetate and aqueous NaHCO3
  3. washThe organic layer was washed with aqueous NaHCO3 (twice) and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-50f2411e559a467ba864b62074379dc4
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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