Acetic Acid → N-(4'-iodophenyl)-2-aminooctane

HRID 21361

Reaction equation

HRID 21361 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.ClC(Cl)C.[CH3:13][C:14](=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:14]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 80932-OctanoneHCID 108934-IodoanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 9927521N-(4'-iodophenyl)-2-aminooctaneYield 88.2%

Procedure

A flask containing 4-iodoaniline (11.0 g, 50.2 mmol) was charged with dry dichloroethane (125 ml), 2-octanone (7.9 ml, 50.0 mmol) and sodium triacetoxyborohydride (13.8 g, 65 mmol). After stirring for 10 minutes, acetic acid (2.9 ml, 50.7 mmol) was added via syringe over a 5 minute period. The reaction was stirred under an N2 atmosphere for 16 hrs. At the end of this period the reaction was quenched by the careful addition of a solution of saturated aqueous ammonium chloride (100 ml). After stirring for 0.5 hr, the reaction was poured over ether (250 ml) and the layers were separated. The ether layer was washed with saturated aqueous ammonium chloride (100 ml), dried (Na2SO4), filtered and evaporated in vacuo. Flash column chromatography (silica, 1:39; EtOAC:hexanes) provided N-(4'-iodophenyl)-2-aminooctane (14.6 g, 88%) as a light yellow oil.

Workup

  1. stirringThe reaction was stirred under an N2 atmosphere for 16 hrs
  2. customAt the end of this period the reaction was quenched by the careful addition of a solution of saturated aqueous ammonium chloride (100 ml)
  3. stirringAfter stirring for 0.5 hr
  4. additionthe reaction was poured over ether (250 ml)
  5. customthe layers were separated
  6. washThe ether layer was washed with saturated aqueous ammonium chloride (100 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-c9b02b03867a4d5a8003dffb26df1f7d
Source dataset
uspto-grants-1995_06
Patent number
US05422114

Linked notes

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