Sodium Iodide → 1-[3-(4-Iodophenoxy)propyl]pyrrolidine

HRID 2264684Notes

Reaction equation

HRID 2264684 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 108944-IodophenolHCID 24758Sodium hydrideHCID 113210281-(3-Chloropropyl)-pyrrolidine

Product 1

HCID 22325891-[3-(4-Iodophenoxy)propyl]pyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4-Iodophenol (2.2 g, 10 mmol) was dissolved in N,N-dimethylformamide (30 mL) under N2, and sodium hydride (0.48 g, 60% dispersion in mineral oil, 12 mmol) was added in portions. 1-(3-Chloropropyl)pyrrolidine (1.77 g, 12 mmol) and sodium iodide (1.8 g, 12 mmol) were added, and the reaction mixture was stirred at 70° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate solution was washed with 1 N HCl (2×). The acidic extracts were made basic with 2 N NaOH, then were extracted with ethyl acetate (2×). All ethyl acetate extracts were combined, dried over MgSO4 and concentrated to give a yellow oil, 2.98 g (90% crude yield). LC-MS (C13H18INO calc'd 331) m/z 332 (M+H).

Workup

  1. washwashed with water
  2. washThe ethyl acetate solution was washed with 1 N HCl (2×)
  3. extractionwere extracted with ethyl acetate (2×)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow oil, 2.98 g (90% crude yield)

Sources & evidence

ORD record
ord-84a6f8ae432f4698ae99d70d4ced5cfa
Source dataset
uspto-grants-2010_12
Patent number
US07855224B2

Reaction notes

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