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

HRID 1503343Notes

Reaction equation

HRID 1503343 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 46926628HCID 46926628, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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].

Workup

  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)

Sources & evidence

ORD record
ord-f539d786fa5b402abca5d6282a2d83b2
Source dataset
uspto-grants-2015_12
Patent number
US09212180B2

Reaction notes

Loading…