Sodium Hydroxide → 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile

The compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized by mixing chloroform (25 mL), tetrahydrofuran (25 mL), 1-benzyl-2-pyrrolidinone (5.16 g, 29.4 mmol), phosphorus oxychloride (5.2 mL) and tin(IV) chloride (1.0 mL), stirring at room temperature for 1.5 hours, and adding anthranilonitrile (3.3 g, 27.9 mmol) in portions. The mixture was then stirred at 50° C. for 5 hours under heating and ice-water (15 mL) and 10% aqueous sodium hydroxide solution was added to make weak alkaline. The organic solvent was removed under reduced pressure and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and condensed under vacuum. The crude product was purified by flash chromatography (chloroform-methanol, 100:1) to yield 7.0 g (91%) Compound 24 as slightly yellow needles; mp 59-61° C.; IR (KBr): 2217, 1628, 1439, 1279 cm−1; 1H NMR (DMSO-d6): δ 7.06-7.69 (m, 9H), 4.83 (s, 2H), 3.46 (t, 2H), 2.60 (t, 2H), 2.10 (m, 2H); 13C NMR (CDCl3): δ 162.8, 156.3, 137.6, 133.7, 132.9, 128.7, 128.3, 127.4, 122.8, 121.7, 118.8, 105.9, 48.3, 47.3, 27.7, 19.6. Anal. Calcd. for C18H17N3(275.35): C, 78.52; H, 6.22; N, 15.26. Found: C, 78.37; H, 6.20; N, 15.17.

1. customThe compound 2-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile (Compound 24) was synthesized
2. stirringThe mixture was then stirred at 50° C. for 5 hours
3. temperatureunder heating
4. customThe organic solvent was removed under reduced pressure
5. extractionthe mixture was extracted with chloroform
6. dry with materialThe extract was dried over anhydrous sodium sulfate and condensed under vacuum
7. customThe crude product was purified by flash chromatography (chloroform-methanol, 100:1)

ORD record

ord-0edaa50437ac404e812d62f234153de7

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693112B2