Hydrochloric Acid → HCID 131721318, compound

The crude benzyl-(2-cyanoethyl)-diethylmalonate from above was dissolved in EtOH (1750 mL) and 5M aqueous HCl (250 mL, 1.25 mol). Pearlman's catalyst containing 20% palladium hydroxide (40 g) was added, and the mixture was hydrogenated in a 1 gallon Hastalloy vessel on a Parr shaker at 50° C. under 40 psi H2 for 22 h. The slurry was filtered through a pad of solkafloc (100 g), and the pad was washed with EtOH (2000 mL). The filtrates were evaporated (25" Hg, bath at 100° C.), and the oily residue was dissolved in water (3500 mL). The aqueous solution was washed with 2:1 by vol hexane-MTBE (1000 mL), and the organic phase was extracted with water (500 mL). The combined aqueous phases were extracted with CH2Cl2 (3×500 mL). The organic extracts were dried over Na2SO4 and evaporated (100° C. at 10 Torr) to an oily residue which crystallized upon cooling to afford benzyl-(3-aminopropyl)-diethylmalonate HCl salt (240.0 g, 70%). 1H NMR (250 MHz, CD3OD) δ 7.97 (br s, 1 H), 7.28-7.10 (m, 5 H), 4.19 (q,J=5.2 Hz, 4 H), 3.23 (s, 2 H), 3.01 (br s, 2 H), 1.90-1.73 (br m, 4 H), 1.23 (t,J=5.2 Hz, 4 H).

1. filtrationThe slurry was filtered through a pad of solkafloc (100 g)
2. washthe pad was washed with EtOH (2000 mL)
3. customThe filtrates were evaporated (25" Hg, bath at 100° C.)
4. dissolutionthe oily residue was dissolved in water (3500 mL)
5. washThe aqueous solution was washed with 2:1 by vol hexane-MTBE (1000 mL)
6. extractionthe organic phase was extracted with water (500 mL)
7. extractionThe combined aqueous phases were extracted with CH2Cl2 (3×500 mL)
8. dry with materialThe organic extracts were dried over Na2SO4
9. customevaporated (100° C. at 10 Torr) to an oily residue which
10. customcrystallized
11. temperatureupon cooling

ORD record

ord-6aa3fa1016ee4ab59b2b9a6642116674

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929243