Potassium Carbonate → 2-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine

HRID 1654024Notes

Reaction equation

HRID 1654024 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]=[CH:23][C:22]=1[CH2:27]Cl>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:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 36138242-(3-Methoxyphenyl)pyrrolidine

Product 1

HCID 233612632-(3-Methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidineYield 91%

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 2-picolyl chloride hydrochloride (3.1 g) at ambient temperature, under nitrogen, with stirring for 65 hrs. The reaction mixture was 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 4.1 g (91%) of 2-(3-methoxyphenyl)-1-(2-pyridinylmethyl)pyrrolidine.

Workup

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

Sources & evidence

ORD record
ord-288e1cdf4a034a90a5157ce5ecbb82d0
Source dataset
uspto-grants-1995_04
Patent number
US05405845

Reaction notes

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