Morpholine → 4-((Morpholin-4-yl)methyl)benzonitrile

HRID 516958

반응식

HRID 516958 반응식
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(Cl)Cl>[O:21]1[CH2:22][CH2:23][N:18]([CH2:2][C:3]2[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=2)[CH2:19][CH2:20]1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 869964-(Bromomethyl)benzonitrile

생성물 1

HCID 2168644-((Morpholin-4-yl)methyl)benzonitrile수율 74%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred suspension of 4-(bromomethyl)benzonitrile (4.00 g, 20 mmol) in DCM (50 ml), at room temperature, triethylamine (4.12 g, 41 mmol) and morpholine (2.67 g, 31 mmol) were added. The reaction mixture was stirred overnight at room temperature. The solution was then diluted with DCM (100 ml) and washed with NaHCO3 saturated aqueous solution (50 ml), the organic phase was separated, dried over magnesium sulphate and solvents evaporated under reduced pressure. The product was purified by column chromatography using a 80 g silica gel cartridge and the following gradient: Solvent A: DCM, Solvent B: MeOH, 1 min hold at 100% A followed by 12 min ramp to 2.5% B and then 5 min hold at 2.5% B. The desired fractions were combined and concentrated to dryness under reduced pressure to obtain the desired product as a white solid (3 g, 14.8 mmol, Yield 72%).

후처리

  1. washwashed with NaHCO3 saturated aqueous solution (50 ml)
  2. customthe organic phase was separated
  3. dry with materialdried over magnesium sulphate and solvents
  4. customevaporated under reduced pressure
  5. customThe product was purified by column chromatography
  6. customMeOH, 1 min
  7. waitfollowed by 12 min ramp to 2.5% B
  8. custom5 min
  9. concentrationconcentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-81417da16c684df18aea44afe691771e
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115088B2

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