Cyclobutanone → 4-(4-(1-Cyanocyclobutylamino)phenyl)butanoic acid

HRID 1192859Notes

Reaction equation

HRID 1192859 reaction equation
C[Si]([C:5]#[N:6])(C)C.[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1.[C:20]1(=O)[CH2:23][CH2:22][CH2:21]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.CC(C)=O.ClCCl>[C:5]([C:20]1([NH:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:13]=2)[CH2:23][CH2:22][CH2:21]1)#[N:6]

Participants

8

Reactant 4

HCID 14496CyclobutanoneHCID 24436Sodium SulfateHCID 270494-(4-Aminophenyl)butanoic acidHCID 82115Trimethylsilyl cyanide

Product 1

HCID 667220494-(4-(1-Cyanocyclobutylamino)phenyl)butanoic acidYield 86%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Trimethylsilyl cyanide (0.50 g, 5 mmol) was added dropwise to a mixture of 4-(4-aminophenyl)-butyric acid (0.537 g, 3 mmol), cyclobutanone (0.35 g, 5 mmol) and sodium sulfate (1 g) in 1,4-dioxane (10 ml). The mixture was stirred for 15 hours. After filtration to eliminate sodium sulfate, the medium was concentrated under vacuum to obtain a brown liquid which was subjected to chromatography (dichloromethane:acetone, 50:50) to yield 4-[4-(1-Cyanocyclobutylamino)-phenyl]-butyric acid (91) (0.665 g, 2.58 mmol, 86%) as a yellowish solid.

Workup

  1. filtrationAfter filtration
  2. concentrationthe medium was concentrated under vacuum
  3. customto obtain a brown liquid which

Sources & evidence

ORD record
ord-58c8d5d5ee1149f0a11005fd26d5ad91
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

Loading…