Ethanol → tert-butyl N-{[4-(aminomethyl)phenyl]methyl}carbamate

Tert-butylphenyl carbonate (2.7 mL, 14.7 mmol) was added dropwise to a solution of p-xylylenediamine (2 g, 14.7 mmol) in ethanol (20 mL) at 80° C. The reaction mixture was refluxed overnight. The solution was then cooled to room temperature and any solids were removed, which leaves a yellow solution. The solution was then concentrated to 10 mL and diluted with water (60 mL). The solution pH was adjusted to 3 with 2M HCl followed by an extraction with dichloromethane (3×75 mL). The water solution pH was then adjusted to pH 12 followed by extraction with dichloromethane (3×75 mL). The organic solutions were combined and washed with sodium bicarbonate (2×75 mL), dried with sodium sulfate, and concentrated down to a white solid. Characterization matches previously published literature (M. A. Ghanem, et al., “Covalent modification of glassy carbon surface with organic redox probes through diamine linkers using electrochemical and solid-phase synthesis methodologies”, Journal of Materials Chemistry, (2008), 18(41), pg 4917-4927).

1. temperatureThe reaction mixture was refluxed overnight
2. customany solids were removed
3. customwhich leaves a yellow solution
4. concentrationThe solution was then concentrated to 10 mL
5. additiondiluted with water (60 mL)
6. extractionfollowed by an extraction with dichloromethane (3×75 mL)
7. extractionfollowed by extraction with dichloromethane (3×75 mL)
8. washwashed with sodium bicarbonate (2×75 mL)
9. dry with materialdried with sodium sulfate
10. concentrationconcentrated down to a white solid
11. customsolid-phase synthesis methodologies”, Journal of Materials Chemistry, (2008), 18(41), pg 4917-4927)

ORD record

ord-5bfb875b4e83407fa5a4c9eefae31918

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921426B2