Acetic Acid → N-((3,4-Dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl)-2-methylpropan-1-amine

Participants

Reaction Steps

To an ice cold mixture of 15 g of 3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde and 67 mL (8 equiv) of isobutylamine in 100 mL of 1,2-dichloroethane was added 50 mL (10 equiv) of acetic acid and 25 g (1.4 equiv) of sodium triacetoxyborohydride. The mixture was allowed to warm and stir overnight then diluted with 500 mL of chloroform and washed with 500 mL of 5N NaOH. The aqueous layer was extracted with 4 additional 100 mL portions of chloroform and the combined extracts dried over magnesium sulfate and concentrated under reduced pressure. After drying under vacuum the product was obtained as clear oil: MS (m+1)=236.2; 1H NMR (400 MHz, CDCl3) 7.0-6.8 (m, 3H), 4.2 (q, 4H), 3.65 (s, 2H), 2.42 (d, 2H), 2.2 (m, 2H), 1.8 (m, 1H), 0.9 (d, 6H).

Provenance & Evidence