Acetic Acid → N-(4-Bromobenzyl)-2,2-dimethoxyethanamine

To an ice-cold solution of 4-bromo-benzaldehyde (10 g, 0.05 mol) and 2,2-dimethoxy-ethylamine (6.8 g, 0.06 mol) in MeOH (200 mL) was added AcOH (2 mL), and the reaction mixture was stirred at RT for 1 h. The reaction mixture was cooled to 0° C. and NaBH4 (6.2 g, 0.15 mol) was added portionwise. The reaction mixture was stirred at RT for 10 h. After completion, The resulting reaction mixture was concentrated under reduced pressure and 10% aqueous NaOH was added. The mixture was extracted with EtOAc, the organic layer separated, dried over Na2SO4, and concentrated under reduced pressure. Purification was done by column chromatography using 100-200 mesh silica gel eluting with 5-15% EtOAc in hexanes to afford N-(4-bromobenzyl)-2,2-dimethoxyethanamine (10 g, 67%) as a pale yellow liquid.

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringThe reaction mixture was stirred at RT for 10 h
3. customAfter completion, The resulting reaction mixture
4. concentrationwas concentrated under reduced pressure and 10% aqueous NaOH
5. additionwas added
6. extractionThe mixture was extracted with EtOAc
7. customthe organic layer separated
8. dry with materialdried over Na2SO4
9. concentrationconcentrated under reduced pressure
10. customPurification

ORD record

ord-be8d3061f31b411a919d5233dcde361e

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334269B2