1-Bromo-3-chloropropane → HCID 46926628、化合物

HRID 1503343ノート

反応式

HRID 1503343 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 46926628HCID 46926628、化合物収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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].

後処理

  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)

出典と根拠

ORDレコード
ord-f539d786fa5b402abca5d6282a2d83b2
出典データセット
uspto-grants-2015_12
特許番号
US09212180B2

反応ノート

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