Sodium Iodide → HCID 66995610, compound

HRID 1928539Notes

Reaction equation

HRID 1928539 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:14][CH2:15]Cl)[CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C>[ClH:1].[ClH:1].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:27][CH2:28][N:29]1[CH2:15][CH2:14][N:4]([CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8421HomoveratrylamineHCID 11430Potassium CarbonateHCID 3025298HCID 3025298, compound

Product 1

HCID 66995610HCID 66995610, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

The reaction mixture of bis-(2-chloroethyl)-(2-phenoxyethyl)amine (0.895 g, 3 mmol), 2-(3,4-dimethoxyphenyl)ethylamine (0.548 g, 3 mmol), potassium carbonate (K2CO3; 1.277 g, 9 mmol), and sodium iodide (NaI; 0.899 g, 6 mmol) in DMF (6 mL) was stirred at 70−80° C. for 5 h, quenched with water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was suspended in 6 N HCl(aq) (pH=3-4) and filtered. The filter cake was then washed with ethyl acetate and ethanol and dried to afford the title compound as a pale white solid (330 mg, 23%). 1H NMR (400 MHz, CD3OD): δ 3.08 (m, 2H), 3.50 (m, 2H), 3.74-3.84 (m, 16H), 4.44 (t, 2H), 6.85-7.05 (m, 6H), 7.32 (m, 2H). m/z 371 [M−2HCl+1]+.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. filtrationfiltered
  6. washThe filter cake was then washed with ethyl acetate and ethanol
  7. customdried

Sources & evidence

ORD record
ord-2c1777c7946844a2a5fdb0aa307e203e
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Reaction notes

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