1,1'-Carbonyldiimidazole → 3-(1-Phenylmethyl-2-pyrrolidinyl)phenyl 2-(4-morpholinyl)ethylcarbamate

To a solution of 3-[1-phenylmethyl-2-pyrrolidinyl]phenol (0.64 g) in dry tetrahydrofuran (20 ml) was added 1,1'-carbonyldiimidazole (0.61 g) at ambient temperature, under nitrogen. The reaction mixture was stirred for 48 hrs, glacial acetic acid (0.50 ml) was added followed by a solution of 4-(2-aminoethyl)morpholine (0.43 ml) in tetrahydrofuran (1.0 ml) and glacial acetic acid (0.20 ml). After 3 hrs, the reaction mixture was poured into saturated sodium bicarbonate solution and ether. The layers were separated, and the aqueous phase was extracted with ether (2 times). The combined organic extracts were washed with saturated sodium bicarbonate and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by radial chromatography, using ether as the eluent. The appropriate fractions were collected and concentrated to give 0.56 g (54%) of product. Recrystallization from ether/petroleum ether gave the analytical sample, mp 74°-77° C.

1. waitAfter 3 hrs
2. customThe layers were separated
3. extractionthe aqueous phase was extracted with ether (2 times)
4. washThe combined organic extracts were washed with saturated sodium bicarbonate and brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by radial chromatography
9. customThe appropriate fractions were collected
10. concentrationconcentrated

ORD-Eintrag

ord-0a95d265ee9d4b2890bd0e326fb6e9ef

Quelldatensatz

uspto-grants-1994_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05338739