Cyclopentanone → 2-(1-cyclopentylpiperidin-4-yloxy)-5-(4-cyanophenyl)pyrimidine

HRID 1666541Notes

Reaction equation

HRID 1666541 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=3)=[CH:16][N:15]=2)[CH2:9][CH2:8]1>[Cl-].[Zn+2].[Cl-].[Na].CO>[CH:1]1([N:7]2[CH2:8][CH2:9][CH:10]([O:13][C:14]3[N:15]=[CH:16][C:17]([C:20]4[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=4)=[CH:18][N:19]=3)[CH2:11][CH2:12]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8452CyclopentanoneHCID 231159714-{2-[(Piperidin-4-yl)oxy]pyrimidin-5-yl}benzonitrile

Product 1

HCID 117395342-(1-cyclopentylpiperidin-4-yloxy)-5-(4-cyanophenyl)pyrimidineYield 89.7%

Reagents, catalysts & solvents 2

HCID 86644332HCID 86644332, compoundCatalystHCID 887MethanolSolvent

Procedure

Cyclopentanone (0.022 mol) and 0.3 N zinc chloride-sodium borocyanide solution (0.55 ml) were added to a methanol solution (3.0 ml) of 2-(piperidin-4-yloxy)-5-(4-cyanophenyl)pyrimidine (46 mg, 0.16 mmol), and stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with chloroform. The organic layer was washed with saturated saline solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified through partitioning thin-layer chromatography (chloroform:methanol=10:1) to obtain the entitled compound (50 mg, 87%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified
  7. customthrough partitioning thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-5dc978c315564b148838fe336c2fca82
Source dataset
uspto-grants-2011_10
Patent number
US08044070B2

Reaction notes

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