Potassium Carbonate → HCID 23361296, compound

HRID 233034Notes

Reaction equation

HRID 233034 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27]Cl)[CH:22]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[CH2:27][C:23]2[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 36138242-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 23361296HCID 23361296, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)pyrrolidine (3.0 g) in dry acetonitrile (70 ml) was added milled potassium carbonate (6.1 g) followed by 3-picolyl chloride hydrochloride (3.1 g) at ambient temperature, under nitrogen, with stirring. The reaction mixture was stirred for 65 hrs, filtered through a pad of celite, and the filter cake was washed with ethyl acetate. The combined filtrates were concentrated, and the residue was purified by flash column chromatography (silica gel, 5% methanol/ether). The appropriate fractions were collected and concentrated to give 3.7 g (83%) of 2-(3-methoxyphenyl)-1-(3-pyridinylmethyl)pyrrolidine.

Workup

  1. stirringThe reaction mixture was stirred for 65 hrs
  2. filtrationfiltered through a pad of celite
  3. washthe filter cake was washed with ethyl acetate
  4. concentrationThe combined filtrates were concentrated
  5. customthe residue was purified by flash column chromatography (silica gel, 5% methanol/ether)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2644e3d3ff6c4bfab08b76ee75f9f796
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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