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

HRID 21431

반응식

HRID 21431 반응식
[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].[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

참가 물질

6

반응물 4

HCID 63651,1-DichloroethaneHCID 80932-OctanoneHCID 108934-IodoanilineHCID 5360545Sodium

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A flask containing 4-iodoaniline (11.0 g, 50.2 retool) was charged with dry dichloroethane (125 ml), 2-octanone (7.9 ml, 50.0 retool) and sodium triacetexyborohydride (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) 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.

후처리

  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

출처 및 근거

ORD 기록
ord-22213ec37f454f329b0a716ed24c074e
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424056

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