Sodium Carbonate → HCID 44140982, compound

HRID 1460484Notes

Reaction equation

HRID 1460484 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][OH:7].[CH3:8][O:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][CH2:15]Br)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.[I-].[Na+]>[OH:7][CH2:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][N:1]1[CH2:15][CH2:14][C:13]1[CH:17]=[CH:18][C:10]([O:9][CH3:8])=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 844271-(2-Bromoethyl)-4-methoxybenzeneHCID 640091L-Prolinol

Product 1

HCID 44140982HCID 44140982, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of (S)-2-pyrrolidinemethanol (3.0 g), 4-methoxyphenethyl bromide (7.0 g), sodium carbonate (3.5 g) and sodium iodide (100 mg) in acetonitrile (40 ml) was heated under reflux for 16 hours and evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water and the organic layer washed with water and extracted with 2M hydrochloric acid. The acidic extract was washed with ethyl acetate, basified with solid sodium carbonate and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a colourless oil, (4.0 g, 57%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. customevaporated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe organic layer washed with water
  6. extractionextracted with 2M hydrochloric acid
  7. extractionThe acidic extract
  8. washwas washed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. extractionThe organic extract
  11. dry with materialwas dried over sodium sulphate
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8a4a2e3fd9804e8498ed2387e3a325b3
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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