Imidazole → 1-[4-(3-Iodopropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

HRID 376963ノート

反応式

HRID 376963 の反応式
O[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:25])[C:13]([N:22]([CH3:24])[CH3:23])([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])=[CH:8][CH:7]=1.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:50]I>C(Cl)Cl>[I:50][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:25])[C:13]([N:22]([CH3:24])[CH3:23])([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])=[CH:8][CH:7]=1

参加物

6

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 193606261-[4-(3-Hydroxypropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

生成物 1

HCID 193605911-[4-(3-Iodopropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
20 °C

実験手順

6.7 g (0.02 mol) of 1-[4-(3-Hydroxypropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one, 3.35 g (0.05 mol) of imidazole and 12.9 g (0.05 mol) of triphenyl phosphine are dissolved in 50 ml of methylene chloride. To the solution are added 10 g (0.039 mol) of iodine and stirred at room temperature (about 20° C.) for 1 hour. 100 ml of methylene chloride is added to the reaction mixture and washed with aqueous solution of sodium sulfite and water, and dried over MgSO4. After distilling off the methylene chloride, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent, and an oily product is obtained. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm]: 1.14 (s, 3H), 2.14 (m, 2H), 2.33 (s, 6H), 2.96 (d, 1H), 3.29 (t, 2H), 3.35-3.40 (m, 2H), 3.42 (d, 1H), 4.21 (br, 1H), 6.56 (d, 2H), 6.89-6.91 (m, 2H), 7.10-7.12 (m, 3H), 8.46 (d, 2H).

後処理

  1. washwashed with aqueous solution of sodium sulfite and water
  2. dry with materialdried over MgSO4
  3. distillationAfter distilling off the methylene chloride
  4. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent
  5. customan oily product is obtained

出典と根拠

ORDレコード
ord-667ae3c1215841b8a68c769a2568c43b
出典データセット
uspto-grants-2000_02
特許番号
US06022906

反応ノート

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