(3-Bromopropyl)benzene → 1-[4-(3-Phenylpropoxy)-1-piperidinyl]ethanone

HRID 1727211Notes

Reaction equation

HRID 1727211 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O.C(O)(C)C.O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 24758Sodium hydrideHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Product 1

HCID 690543231-[4-(3-Phenylpropoxy)-1-piperidinyl]ethanoneYield 27.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent3×

Procedure

1-Acetylpiperidin-4-ol (Preparation 193, 8 g, 60 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to a stirred suspension of sodium hydride (50% wt dispersion in oil, 3.68 g, 80 mmol) in N,N-dimethylformamide (50 ml) at room temperature under nitrogen. After stirring the reaction mixture for 4 hours, 1-bromo-3-phenylpropane (12.94 g, 65 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to the solution at 0° C. and the reaction mixture was stirred for a further 4 h. The solution was diluted with isopropyl alcohol (20 ml) and water (100 ml) and then evaporated to give a semi solid. Water (100 ml) was added and the solution was extracted with petroleum ether (3×100 ml). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give an orange oil (4.3 g, 27%).

Workup

  1. stirringthe reaction mixture was stirred for a further 4 h
  2. customevaporated
  3. customto give a semi solid
  4. extractionthe solution was extracted with petroleum ether (3×100 ml)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d4a94d44e824426a692d6139dca7bda
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

Loading…