Anisole → HCID 4993578, compound

HRID 322153Notes

Reaction equation

HRID 322153 reaction equation
O[C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+].[C:20]1([O:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:27][O:26][C:20]1[CH:25]=[CH:24][C:23]([C:2]2([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]2)=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 7519AnisoleHCID 14798Sodium HydroxideHCID 963874-Phenylpiperidin-4-olHCID 6451240Aluminum(III) Chloride

Product 1

HCID 4993578HCID 4993578, compound

Procedure

4-Hydroxy-4-phenylpiperidine (5.00 g, 28.2 mmol, 1.00 equiv, Aldrich) was added to a suspension of AlCl3 (18.8 g, 141 mmol, 5.00 equiv) in anhydrous anisole (100 mL). The mixture was stirred at room temperature for 1 hour and then heated to 50° C. for 3.5 hours. It was cooled to room temperature and poured cautiously into ice-water. The mixture was basified to pH 11 by addition of 6M aqueous NaOH, and extracted with EtOAc (3×75 mL). The combined organic solutions were applied directly to a flash chromatography column, which was eluted with CH2Cl2—NH3 in MeOH (0.67M), 4:1 to afford 1.683 g (22%) of light yellow oil, which was characterized spectroscopically.

Workup

  1. temperatureheated to 50° C. for 3.5 hours
  2. temperatureIt was cooled to room temperature
  3. extractionextracted with EtOAc (3×75 mL)
  4. washwas eluted with CH2Cl2—NH3 in MeOH (0.67M), 4:1
  5. customto afford 1.683 g (22%) of light yellow oil, which

Sources & evidence

ORD record
ord-eee5593bf2d245a1ad88c008508f919e
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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