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

HRID 376963노트

반응식

HRID 376963 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-667ae3c1215841b8a68c769a2568c43b
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022906

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