Hydrochloric Acid → N-Ethyl-4-chlorobenzylamine

N-(4-chlorobenzyl)acetamide (2.337 g, 12.726 mmol) was dissolved in THF (100 ml) and was cooled to zero degrees under argon atmosphere. (Methylthio)methane compound with borane (1:1) (2.417 g, 31.815 mmol) was added and the mixture was refluxed overnight at RT. HCl (15 ml, 10%) was gently added and was stirred overnight. The solvent was removed by evaporation. Diethyl ether (20 ml) was added and the product was extracted to the water phase by K2CO3 (3×15 ml). The aqueous phase was acidified by HCl (10 ml, 10%) and the product was extracted to the organic phase by EtOAc (3×15 ml). The organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 0.938 g of N-(4-chlorobenzyl)-N-ethylamine (yield 43.4%).

1. temperaturewas cooled to zero degrees under argon atmosphere
2. customThe solvent was removed by evaporation
3. additionDiethyl ether (20 ml) was added
4. extractionthe product was extracted to the water phase by K2CO3 (3×15 ml)
5. extractionthe product was extracted to the organic phase by EtOAc (3×15 ml)
6. dry with materialThe organic phase was dried (MgSO4)
7. customthe solvent was removed by evaporation

ORD record

ord-d3cc7e49d23c43f7a2f74d195e7073a7

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07351858B2