1,2-Dichloroethane → 7-Phenyl-isoquinoline-5-sulfonic acid [2-(3-naphthalen-1-yl-propylamino)-ethyl]-amide dihydrochloride

Participants

Reaction Steps

Stir a mixture of 7-phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide (0.25 mmol, 1.0 eq) and 3-naphthalen-1-yl-propionaldehyde (0.25 mmol, 1.0 eq) in 1,2-dichloroethane (DCE) (2.0 mL) at room temperature for six (6) hours, and then add sodium triacetoxyborohydride (0.6 mmol, 2.4 eq). Stir overnight, then dilute the mixture with CH3OH, and apply to a cation exchange column (10 g), wash with a mixture of, CH3OH and CH2Cl2 (1:1), then NH3 (2.0 M in CH3OH). Purify the residue on silica gel (gradient 10% CH3OH in CH2Cl2) to give 100 mg the free amine product as oil. Dissolve the free amine in CH3OH (15 mL) and treat dropwise with 37% HCl aqueous solution (1.0 mL) with stirring. Concentrate the resultant solution and dried under vacuum at 37° C. to give the title compound as a white powder. 1H NMR (DMSO-d6, 400 MHz): 9.65 (1H, s), 8.85 (2H, br), 8.75 (1H, s), 8.69 (1H, d, J=6.0 Hz), 8.64 (1H,s), 8.53 (1H, t, J=6.0 Hz), 8.07 (1H, d, J=8.0 Hz), 7.91 (2H, d, J=7.6 Hz), 7.78 (1H, d, J=8.0 Hz), 7.49-7.61(4H, s), 7.46 (1H, d, J=7.6 Hz), 7.35 (1H, d, J=7.2 Hz), 3.12-3.15 (2H, m), 3.07 (2H, t, J=7.6 Hz), 2.95-3.02 (4H, m), 1.93-1.99 (2H, m). IS-MS, m/e 582.58 (m+1)

Provenance & Evidence