Water → HCID 69055073, compound

HRID 1727207Notes

Reaction equation

HRID 1727207 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+].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.O>CN(C)C=O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 96024-Fluorobenzyl chlorideHCID 24758Sodium hydrideHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Product 1

HCID 69055073HCID 69055073, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

1-Acetylpiperidin-4-ol (Preparation 193, 10 g, 70 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to a stirred suspension of sodium hydride (50% wt dispersion in oil, 3.8 g, 80 mmol) in N,N-dimethylformamide (50 ml) at room temperature under nitrogen. After stirring the reaction mixture for 3 hours, 4-fluorobenzyl chloride (10.1 g, 70 mmol) in N,N-dimethylformamide (50 ml) was added dropwise and the reaction mixture was stirred for a further 4 h. The reaction mixture was filtered and the filtrate was evaporated to give an orange oil. Water was added and the mixture was extracted with petroleum ether (3×100 ml) and then with diethyl ether (3×100 ml). The combined organic extracts were washed with sodium hydroxide solution (1 M, 3×100 ml), before drying (Na2SO4) and concentrating to give the title compound as an oil (10.1 g, 99%).

Workup

  1. stirringthe reaction mixture was stirred for a further 4 h
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. customto give an orange oil
  5. extractionthe mixture was extracted with petroleum ether (3×100 ml)
  6. washThe combined organic extracts were washed with sodium hydroxide solution (1 M, 3×100 ml)
  7. dry with materialbefore drying (Na2SO4)
  8. concentrationconcentrating

Sources & evidence

ORD record
ord-9568ea7f245f4351bfa037f640ab820f
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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