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

HRID 21431

反応式

HRID 21431 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-22213ec37f454f329b0a716ed24c074e
出典データセット
uspto-grants-1995_06
特許番号
US05424056

関連ノート

読み込み中…