Ammonium Chloride → (+/-)-2-Methyl-3-((2-amino)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

Participants

Reaction Steps

A mixture of (±)-2-Methyl-3-((2-nitro)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide (80 mg), ammonium chloride (53 mg), and zinc powder (106 mg) in 6 ml of EtOH—H2O (9-10) was stirred overnight, and then filtered through a layer of zeolite. The filtercake was rinsed with methanol (5 ml×3), and the combined filtrate was concentrated under reduced pressure. The residue was then partitioned between of dichloromethane and saturated aq. sodium bicarbonate (6 ml each). The aqueous layer was then extracted with dichloromethane (6 ml). The organic layer was washed with brine and then concentrated to yield (±)-2-Methyl-3-((2-amino)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide as a resin: MS (m+1)=460.3; 1H NMR (500 MHz, CDCl3) 0.95 (m, 6H), 1.15 (dd, 3H), 2.00 (m, 1H), 2.25 (m, 2H0, 2.60 (q, 1H), 2.70 (q, 1H), 2.90 (m, 1H), 3.05 (m, 1H), 3.10 (m, 1H), 3.20 (q, 1H), 3.35 (q, 1H), 3.45 (q, 1H), 3.70 (m, 2H), 4.25 (m, 2H), 4.35 (m, 2H), 4.55 (m, 2H), 6.6-7.2 (m, 4H), 6.8-7.0 (m, 2H).

Provenance & Evidence