Dimethylformamide → 3-(2-Bromophenoxy)-1-(2-methoxyethyl)pyrrolidine

HRID 1245861Notes

Reaction equation

HRID 1245861 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1.Br[CH2:15][CH2:16][O:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:1][C:2]1[CH:13]=[CH:12][CH:11]=[CH:10][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:15][CH2:16][O:17][CH3:18])[CH2:6]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 219143993-(2-Bromophenoxy)pyrrolidine

Product 1

HCID 219143843-(2-Bromophenoxy)-1-(2-methoxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(2-Bromophenoxy)pyrrolidine (1.23 g), 1-bromo-2-methoxyethane (0.526 ml) and potassium carbonate (842 mg) were mixed with dimethylformamide (50 ml) and stirred for two days. The mixture was added to water (100 ml). The mixture was extracted with diethyl ether (3×50 ml), washed with water (2×50 ml), brine (2×30 ml), dried (MgSO4) and concentrated in vacuo. Purification was achieved using cation exchange chromatography eluting with ammonia/methanol/dichloromethane mixtures yielding product as a clear oil (0.8 g).

Workup

  1. extractionThe mixture was extracted with diethyl ether (3×50 ml)
  2. washwashed with water (2×50 ml), brine (2×30 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washeluting with ammonia/methanol/dichloromethane mixtures

Sources & evidence

ORD record
ord-ba1dbbf0f40b4612bb88e784533754ff
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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