Sodium Iodide → HCID 69253831, compound

HRID 902626Notes

Reaction equation

HRID 902626 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14]Br)[CH:6]=1.[C:17]1([C@@H:23]([CH3:26])[CH2:24][NH2:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][NH:25][CH2:24][C@@H:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:26])[CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1547949(R)-(+)-beta-MethylphenethylamineHCID 10565189Methyl [3-(3-bromopropoxy)phenyl]acetate

Product 1

HCID 69253831HCID 69253831, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

[3-(3-Bromo-propoxy)-phenyl]-acetic acid methyl ester (11.48 g, 0.04 mole) in acetonitrile (300 mL) was added dropwise over 45 minutes to a mixture of (R)-2-Phenyl-propylamine (1.3 eq., 7.04 g, 0.052 mole), sodium iodide (18.0 g, 0.12 mole), and potassium carbonate (16.6 g, 0.12 mole) in acetonitrile (2000 mL). The mixture was stirred five days. The reaction mixture was filtered and the filter cake washed with acetonitrile (500 mL). The acetonitrile was evaporated and the residue dissolved in methylene chloride and washed with water(2×), dried over magnesium sulfate, filtered and evaporated. The resulting residue was purified by silica gel chromatography (using 3% to 10% methanol/methylene chloride as elutant) to give the title compound (10.19 g, 75%). MS (ESI) 342 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake washed with acetonitrile (500 mL)
  3. customThe acetonitrile was evaporated
  4. dissolutionthe residue dissolved in methylene chloride
  5. washwashed with water(2×)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting residue was purified by silica gel chromatography (using 3% to 10% methanol/methylene chloride as elutant)

Sources & evidence

ORD record
ord-464ffdda8cc049648404684c995c40b8
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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