1-Benzyl-4-piperidone → HCID 59756817, compound

HRID 1663330Notes

Reaction equation

HRID 1663330 reaction equation
[Br:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][N:3]=1.CC([Mg]Cl)C.[CH2:14]([N:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O1CCCC1>[CH2:14]([N:21]1[CH2:26][CH2:25][C:24]([OH:27])([C:7]2[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:23][CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 8171022,3-DibromopyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 59756817HCID 59756817, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10 g (42 mmol) 2,3-dibromopyridine in 210 ml dry tetrahydrofuran at room temperature were added 22 ml (44 mmol) 2-propylmagnesium chloride solution (2.0 M in tetrahydrofuran). The reaction mixture was stirred for 1 h at room temperature. A solution of 7.9 g (44 mmol) 1-benzyl-4-piperidone in 40 ml tetrahydrofuran was added, and stirring was continued for 16 h. The reaction mixture was quenched with water, basified to pH 9 with aqueous 2 M sodium hydroxide solution and extracted with tert-butyl methyl ether (3×). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. Flash-chromatography (aminopropyl-modified silica gel) gave the title compound (3.4 g, 23%) as an orange amorphous solid.

Workup

  1. stirringstirring
  2. waitwas continued for 16 h
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with tert-butyl methyl ether (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d40779ccc3e34acdad6feee107d5cd49
Source dataset
uspto-grants-2011_10
Patent number
US08034937B2

Reaction notes

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