Acetic Acid → N-(3-Iodobenzyl)-N,N-dimethylamine

Temperature

0 °C

To a cold (0° C.) solution of 3-iodo-benzaldehyde (3 g, 12.9 mmol) in anhydrous dichloromethane (130 ml) were added acetic acid (1.9 ml) and N,N-dimethylacetamide. The yellow solution is stirred 10 minutes at 0° C. and sodium triacetoxyborohydride (6.85 g, 32.33 mmoles) is added by portions. The resulting mixture is stirred at room temperature for 90 minutes and evaporated to dryness under reduced pressure. Ethyl acetate and a saturated aqueous hydrogen carbonate solution were added to the residue and the two layers were separated The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to yield (3-iodo-benzyl)-dimethyl-amine (3.05 g, 90%) as a brown oil.

1. stirringThe resulting mixture is stirred at room temperature for 90 minutes
2. customevaporated to dryness under reduced pressure
3. additionEthyl acetate and a saturated aqueous hydrogen carbonate solution were added to the residue
4. customthe two layers were separated The organic phase
5. washwas washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum

ORD record

ord-f043558804914f0eaa1eb00ec10c1e75

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846712B2