HCID 9795992, compound → HCID 57672014, compound

HRID 657611Notes

Reaction equation

HRID 657611 reaction equation
[C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:17][C@@H:16]([CH3:18])[CH2:15][C@H:14]([CH3:19])[CH2:13]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:22][Mg]Br>O1CCCC1>[OH:3][C:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][C@@H:14]([CH3:19])[CH2:15][C@H:16]([CH3:18])[CH2:17]2)=[CH:6][CH:5]=1)([CH3:22])[CH3:2]

Participants

4

Reactant 2

HCID 9795992HCID 9795992, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57672014HCID 57672014, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-1-[3-(4-acetylphenoxy)propyl]-3,5-dimethylpiperidine (289 mg) in tetrahydrofuran (1 mL) is stirred at room temperature under anhydrous atmosphere and a 2.61 M solution of methylmagnesium bromide in tetrahydrofuran (400 μL) is added dropwise. The mixture is stirred at room temperature for 3 h and quenched with a saturated aqueous solution of ammonium chloride. The solution is extracted with ethyl acetate and the combined extracts washed with water, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with dichloro-methane/methanol 95/5 as eluent. Fractions containing the expected product are pooled and salted with 20 mg of oxalic acid to give 70 mg of trans-1-{3-[4-(1-hydroxy-1-methylethyl)-phenoxy]propyl}-3,5-dimethylpiperidine, oxalate as a pale yellow solid.

Workup

  1. customquenched with a saturated aqueous solution of ammonium chloride
  2. extractionThe solution is extracted with ethyl acetate
  3. washthe combined extracts washed with water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography over silica gel with dichloro-methane/methanol 95/5 as eluent
  7. additionFractions containing the expected product

Sources & evidence

ORD record
ord-41bfa7b5a2e843e49697c89efef1525e
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

Loading…