1,1-Dichloroethane → N-(4'-iodophenyl)-2-aminooctane

HRID 1729003Notes

Reaction equation

HRID 1729003 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 4

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

Product 1

HCID 9927521N-(4'-iodophenyl)-2-aminooctaneYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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 retool) and sodium triacetoxyborohydride (13.8 g, 65 retool). After stirring for 10 minutes, acetic acid (2.9 ml, 50.7 retool) 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) andthe 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-amino octane (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) andthe layers
  5. customwere 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-53dd9d0d7f3244669e06868efc5502a6
Source dataset
uspto-grants-1994_07
Patent number
US05330740

Reaction notes

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