Water → HCID 53482622, compound

HRID 420651Notes

Reaction equation

HRID 420651 reaction equation
C(O[C:4]([C:6]1([CH2:16][CH2:17]OC)[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH3:14])[C:8](=[O:15])[CH2:7]1)=[O:5])C.[F:20][C:21]([F:31])([F:30])[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1.[Cl-].C[Al+]C.O>C1(C)C=CC=CC=1.CCCCCC>[CH2:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:5])[N:27]([C:26]3[CH:28]=[CH:29][C:23]([O:22][C:21]([F:20])([F:30])[F:31])=[CH:24][CH:25]=3)[CH2:17][CH2:16]2)[CH2:7][C:8]1=[O:15])[CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 6008484-(Trifluoromethoxy)anilineHCID 16686359Dimethylalumanylium chlorideHCID 58478408HCID 58478408, compound

Product 1

HCID 53482622HCID 53482622, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

4-(2-Methoxy-ethyl)-2-oxo-1-propyl-piperidine-4-carboxylic acid ethyl ester (0.205 g) and 4-(trifluormethoxy)aniline (0.268 g) were dissolved in toluene (15 ml) under an argon atmosphere at RT. Dimethylaluminium chloride in hexane (1 molar in hexane, 3.02 ml) was added and the mixture was refluxed over night. The reaction mixture was then cooled to RT, water (1 ml) was added and the mixture was stirred at RT for 15 minutes. The solvent was removed in vacuo, the residue adsorbed on silica gel and purified by flash chromatography on silica gel (eluents: AcOEt/CH2Cl2, gradient from 0 to 50% then with AcOEt/heptane: 70%) to give the desired material (0.072 g) as a viscous light yellow oil. MS (ESI): 371.2 (MH−).

Workup

  1. temperaturethe mixture was refluxed over night
  2. customThe solvent was removed in vacuo
  3. custompurified by flash chromatography on silica gel (eluents

Sources & evidence

ORD record
ord-6c560f906e374b90a1de73caf7ca1809
Source dataset
uspto-grants-2012_01
Patent number
US08097634B2

Reaction notes

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