Acetic Anhydride → HCID 68998822, compound

3-{(S)-2-[4-(4-Chloro-phenoxy)-phenoxymethyl]-pyrrolidin-1-yl}-propylamine (50 mg, 0.139 mmol) and Diisopropylethyl amine (26.9 mg, 0.208 mmol) were taken into dichloromethane (2 ml). Acetic Anhydride (0.016 mL, 0.166 mmol) was then added to the reaction mixture. The reaction was left at room temperature for 24 h. The mixture was then partitioned between sodium bicarbonate (aq) and dichloromethane. The aqueous layer was washed with dichloromethane (3×). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to dryness. The crude compound was purified by flash silica chromatography (40:1 silica ratio, eluted with 5% methanol in dichloromethane, followed by 10% methanol in dichloromethane). The pure product was then taken into 4M HCl in dioxane and left at room temperature for 3 h. The mixture was concentrated to dryness under vacuum to yield the title product (22 mg, 0.05 mmol, 36%); LCMS; m/z 404 (m+1 of free amine); 1H NMR (400 MHz, DMSO-d6) δ 1.8-2.05 (m, 7H), 2.20-2.27 (m, 1H), 3.07-3.18 (m, 3H), 3.43-3.52 (m, 1H), 3.54-3.57 (m, 1H), 4.28-4.38 (m, 2H), 4.88 (s, 3H), 6.93-6.96 (m, 2H), 7.06 (s, 4H), 7.39-7.41 (m, 2H), 8.06 (m, 1H)

1. customThe mixture was then partitioned between sodium bicarbonate (aq) and dichloromethane
2. washThe aqueous layer was washed with dichloromethane (3×)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated to dryness
6. customThe crude compound was purified by flash silica chromatography (40:1 silica ratio, eluted with 5% methanol in dichloromethane, followed by 10% methanol in dichloromethane)
7. waitleft at room temperature for 3 h
8. concentrationThe mixture was concentrated to dryness under vacuum

ORD record

ord-f829caebb8f04df58ff1d886206e809c

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402684B2