Methyl iodide → HCID 67214782, compound

HRID 2421384Notes

Reaction equation

HRID 2421384 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1.[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Br:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[CH3:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67215191HCID 67215191, compound

Product 1

HCID 67214782HCID 67214782, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2R)-2-[(2-Bromophenoxy)methyl]pyrrolidine (1.84 g), potassium carbonate (1.09 g) and methyl iodide (0.49 ml) were stirred in dimethylformamide (10 ml) for 2 h at room temperature. The mixture was concentrated in vacuo and water added (50 ml). The mixture was extracted with diethyl ether (3×30 ml). The organic portions were combined and washed with water (2×20 ml), brine (2×20 ml) and dried (MgSO4) and concentrated in vacuo yielding the title compound as a pale orange oil (0.75 g).

Workup

  1. concentrationThe mixture was concentrated in vacuo and water
  2. additionadded (50 ml)
  3. extractionThe mixture was extracted with diethyl ether (3×30 ml)
  4. washwashed with water (2×20 ml), brine (2×20 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1498f12c3cd94229b90c3806443385b2
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

Loading…