1-Bromo-3-chloropropane → HCID 46926628, 화합물

HRID 1503343노트

반응식

HRID 1503343 반응식
Br.[C:2]([CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25]Cl.[C:27]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)#[N:28]>CN(C=O)C>[C:2]([CH:10]1[CH2:15][CH2:14][N:13]([CH2:23][CH2:24][CH2:25][O:35][C:32]2[CH:33]=[CH:34][C:29]([C:27]#[N:28])=[CH:30][CH:31]=2)[CH2:12][CH2:11]1)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 20530718Phenyl(piperidin-4-yl)methanone hydrobromide

생성물 1

HCID 46926628HCID 46926628, 화합물수율 78%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Benzoylpiperdine hydrobromide (2.70 g, 10 mmol) was combined with K2CO3 (6.9 g, 50 mmol) in DMF (˜40 mL), followed by 1-bromo-3-chloropropane (1.55 g, 10 mmol). The reaction progress was monitored by LC-MS and upon completion of the reaction (˜2 h) 4-cyanophenol (1.3 g, 11 mmol) was added and the reaction allowed to stir overnight. The mixture was poured onto water and extracted with ethyl acetate, washed with brine and dried over Na2SO4. The volatiles were removed under reduced pressure and the crude mixture purified on silica gel (0-100% EtOAc in hexanes) to give 2.71 g (78% yield over 2 steps) of 4-(3-(4-benzoylpiperidin-1-yl)propoxy)benzonitrile: LC-MS (>98%) m/z=349.2 [M+H].

후처리

  1. additionwas added
  2. additionThe mixture was poured onto water
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe volatiles were removed under reduced pressure
  7. customthe crude mixture purified on silica gel (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-f539d786fa5b402abca5d6282a2d83b2
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212180B2

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