Cyclobutylamine → N-{1-[2-(4-Fluorophenyl)pyridin-4-yl]ethyl}cyclobutaneamine

HRID 1026759Notes

Reaction equation

HRID 1026759 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([C:19](=O)[CH3:20])[CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[C:17]([CH:19]([NH:5][CH:1]3[CH2:4][CH2:3][CH2:2]3)[CH3:20])[CH:16]=[CH:15][N:14]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 75645CyclobutylamineHCID 516892Sodium BicarbonateHCID 866904831-[2-(4-Fluorophenyl)pyridin-4-yl]ethanone

Product 1

HCID 86690484N-{1-[2-(4-Fluorophenyl)pyridin-4-yl]ethyl}cyclobutaneamineYield 97.8%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent2×

Procedure

Titanium(IV) isopropoxide (1.85 g) was added to a solution of cyclobutylamine (930 mg) in methanol (10 mL), and the mixture was stirred at room temperature for 10 min. A solution of 1-[2-(4-fluorophenyl)pyridin-4-yl]ethanone (350 mg) in methanol (5 mL) was added thereto and the mixture was stirred at room temperature overnight. Saturated sodium hydrogen carbonate solution was added to the reaction mixture, which was then filtered through Celite, and the solvent was distilled off under reduced pressure. After extracting with chloroform, the organic phase was separated out, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=98:2-80:20) to afford the title compound (430 mg).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationwas then filtered through Celite
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionAfter extracting with chloroform
  5. customthe organic phase was separated out
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=98:2-80:20)

Sources & evidence

ORD record
ord-0e2248f51d54413a915473444cabf1c7
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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