2-Bromopropiophenone → 2-{[4-(2-Hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone

HRID 967809

반응식

HRID 967809 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.Br[CH:12]([CH3:21])[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>CN(C=O)C>[OH:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([NH:1][CH:12]([CH3:21])[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])=[CH:3][CH:4]=1

참가 물질

4

반응물 2

HCID 164522-BromopropiophenoneHCID 669044-Aminophenethyl alcohol

생성물 1

HCID 222913492-{[4-(2-Hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-aminophenethyl alcohol (690 mg, 5.0 mmol), 2-bromopropiophenone (2.1 g, 10 mmol) potassium carbonate (690 mg, 5.0 mmol) in DMF (50 mL) was stirred at ambient temperature for 3 days. The mixture was partitioned between ethyl acetate and water. The combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1) to afford the title compound quantitatively as yellow oil: 1H-NMR (CDCl3) δ 1.49 (2H, d, J=6.9 Hz), 2.74 (2H, t, J=6.4 Hz), 3.79 (2H, t, J=6.4 Hz), 4.65 (1H, br), 5.11 (1H, m), 6.65 (2H, d, J=8.4 Hz), 7.05 (2H, d, J=8.6 Hz), 7.48-7.65 (3H, m), 8.03 (2H, d, J=7.2 Hz).

후처리

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-e0161847907e49918ace3ffa7c8d46f4
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06956050B2

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