Hydrochloric Acid → 1-(Phenylmethyl)-1H-1,2,3-triazole-4-ethanamine

A reaction mixture comprising tert-butyl but-3-yn-1-ylcarbamate (306 mg, 1.808 mmol), (azidomethyl)benzene (241 mg, 1.808 mmol), copper (II) acetate (32.8 mg, 0.181 mmol) and Sodium L-ascorbate (71.6 mg, 0.362 mmol) in tert-butanol (25 ml)/water (25 ml) was stirred for 18 hours at room temperature. The reaction mixture was acidified to pH1 using 6M HCl and then saturated with solid NaCl. The reaction mixture was concentrated under reduced pressure. The remaining mixture was diluted with ethyl acetate. The organics were separated and dried over MgSO4, filtered, and the solvent concentrated under reduced pressure to afford an orange oil. The oil was loaded on to a 10 g SCX2 cartridge. The cartridge was washed with water and methanol. Product was then eluted with 2M ammonia in methanol. The solution was then concentrated under pressure to afford the title compound.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionThe remaining mixture was diluted with ethyl acetate
3. customThe organics were separated
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationthe solvent concentrated under reduced pressure
7. customto afford an orange oil
8. washThe cartridge was washed with water and methanol
9. washProduct was then eluted with 2M ammonia in methanol
10. concentrationThe solution was then concentrated under pressure

ORD record

ord-ff521f441e4c4b558818b0848d52519b

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409895B2