Pyridine → HCID 9905985, compound

(±)-cis-2-(1-pyrrolidinyl)cyclohexylamine (5 gm) was combined with pyridine (1.2 gm), chloroform (200 ml), 3,4-dichlorophenylacetic acid (9.15 gm), and dicyclohexylcarbodiimide (12.3 gm) and the mixture was stirred for 12 hr at room temperature. The mixture was filtered, the precipitate was washed with ether (100 ml) and the filtrate and ether wash were combined. The organic solution was diluted with ether (200 ml) and extracted with 10% citric acid in water (300 ml). The acid layer was washed with ether (2×200 ml), then treated with excess concentrated aqueous ammonia until basic. The resulting mixture was extracted with methylene chloride (2×200 ml) and the combined organic extracts were washed with water (2×50 ml) and concentrated on a rotary evaporator. The resulting white solid was combined with tetrahydrofuran (25 ml) and added dropwise to a solution of AlH3 in tetrahydrofuran (76.2 ml of a 0.665M solution) at room temperature. After the addition, the mixture was poured into 15% NaOH and the resulting mixture was extracted with ether (3×100 ml). The ether was removed on a rotary evaporator and the residue was dissolved in ethanol (100 ml). The ethanol was removed on a rotary evaporator and the residue was converted to the hydrogen bromide salt which was recrystallized from ethanol. Analytical data are reported in Table I.

1. filtrationThe mixture was filtered
2. washthe precipitate was washed with ether (100 ml)
3. washthe filtrate and ether wash
4. additionThe organic solution was diluted with ether (200 ml)
5. extractionextracted with 10% citric acid in water (300 ml)
6. washThe acid layer was washed with ether (2×200 ml)
7. additiontreated with excess concentrated aqueous ammonia until basic
8. extractionThe resulting mixture was extracted with methylene chloride (2×200 ml)
9. washthe combined organic extracts were washed with water (2×50 ml)
10. concentrationconcentrated on a rotary evaporator
11. additionadded dropwise to a solution of AlH3 in tetrahydrofuran (76.2 ml of a 0.665M solution) at room temperature
12. additionAfter the addition
13. additionthe mixture was poured into 15% NaOH
14. extractionthe resulting mixture was extracted with ether (3×100 ml)
15. customThe ether was removed on a rotary evaporator
16. dissolutionthe residue was dissolved in ethanol (100 ml)
17. customThe ethanol was removed on a rotary evaporator
18. customwas recrystallized from ethanol

ORD record

ord-f0e7299f899f4353a3ca20b9796f6ab6

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739158