Ethyl Acetate → HCID 19385511, compound

HRID 2399381Notes

Reaction equation

HRID 2399381 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][Cl:10])[CH:4]=1.[CH3:11][CH:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH3:13].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O>[CH3:13][CH:12]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]1[CH2:26][CH2:25][CH:24]([CH2:2][C:3]2[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=2)[CH2:9][Cl:10])[CH2:23][CH2:22]1)[CH3:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 12275Benzene, 1,3-bis(chloromethyl)-HCID 17875125HCID 17875125, compound

Product 1

HCID 19385511HCID 19385511, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A biphasic solution of α,α'-dichloro-m-xylene (2.40 g, 0.0137 mol), N-[2-(1-methylethoxy)phenyl]piperidine (3.00 g, 0.0137 mol), sodium carbonate (2.19 g, 0.020 mol), ethyl acetate (20 mL), and H2O (20 mL) was refluxed for 3 h. The organic layer was separated, dried (MgSO4), filtered, and evaporated to an oil. The residue was chromatographed on silica gel using chloroform as eluant to give 3-[[1-[2-(1-methylethoxy)phenyl]-4-piperidinyl]methyl]benzyl chloride (1.25 g, 25%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to an oil
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f7ebdb9c205740718c58511ba459e3df
Source dataset
uspto-grants-1995_09
Patent number
US05449677

Reaction notes

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