1-aminopyrrolidin-2-one hydrochloride

4-Chlorobutyryl chloride (57 mL, 510 mmol) is added to a solution of benzophenone hydrazone (100 g, 510 mmol) and pyridine (41 mL, 510 mmol) in anhydrous CH2C12 (520 mL) under nitrogen at a rate that maintained a gentle reflux throughout the addition. The mixture is stirred for 0.5 h and poured into water (1 L). The layers are separated and the organic layer is washed with brine, dried (NA2S04), filtered, and concentrated in vacuo to yield 4-chloro-butyric acid benzhydrylidene-hydrazide as a residue. MS ES+ M/E 301. 1 (M+1). This residue is dissolved in THF (1.5 L), and the solution cooled in an ice-water bath, treated with portions of NaH (60percent suspended in mineral oil, 20 g, 498 mmol) and stirred for 1 h. To the mixture is added saturated aqueous NH4CL solution (1 L) and EtOAc (1 L). The layers are separated and the organic solution washed with brine, dried (NA2SO4), filtered and concentrated in vacuo to yield 1- (BENZHYDRYLIDENEAMINO) pyrrolidin-2-one as a residue. APOS;H NMR (CDCl3) : 8 7.58-7. 62 (m, 2H), 7.39-7. 46 (m, 4H), 7.29-7. 36 (m, 4H) 3.31 (t, J = 7 Hz, 2H), 2.32 (t, J = 7 Hz, 2H), 1.91 (quintet, J = 7 Hz, 2H); MS ES+ M/E 265.1 (M+1). This residue is suspended in water (3 L), treated with concentrated HC1 solution (80 mL), and heated to reflux for 1.5 h. The reaction is cooled to RT and extracted twice with CH2CL2. The aqueous portion is concentrated in vacuo followed by azeotropic removal of water with three portions of absolute ethanol and three portions of toluene to yield the title compound, 56 g (81percent), as a white solid. 'H NMR (DMSO-d6): 8 3.58 (t, J = 7 Hz, 2H), 2.33 (t, J = 7Hz, 2H), 2.04 (quintet, J = 7 Hz, 2H), TOF MS ES+ exact mass calculated for C4H8N2 (M+): M/Z = 100.0637. Found: 100.0641.

Molecular Weight:136.58
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:136.0403406
Monoisotopic Mass:136.0403406
Topological Polar Surface Area:46.3
Heavy Atom Count:8
Complexity:91.7
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes