1-(3-CHLOROPROPYL)-PYRROLIDINE

Intermediate 5: 1-(3-Chloro-propyl)-pyrrolidine; Pyrrolidine (10g, 0.14mol), acetone (28ml), 5M NaOH solution (21ml) and 1-bromo-3-chloropropane (24.4g, 0.15mol) were stirred together under N2 for 8hours. The organic layer was separated and concentrated in vacuo. The crude product was purified by vacuum distillation (b.p. 90°C/30mbar) to give the title compound (11.7g, 57percentth) as a colourless oil.1H NMR (400MHz, CDCl3) δ3.67 (t, 2H), 2.49 (t, 2H), 2.46-2.37 (m, 4H), 1.88 (p, 2H), 1.72-1.64 (m, 4H).Example 4 General procedure: A 1.00 g (16.9 mmol) amount of N-methylbenzylamine, Nmethyl-N-phenylethylamine, or pyrrolidine was dissolved in 25 mL of DMF. After addition of potassium carbonate (4.6 g, 33.0 mmol), the resulting mixture was heated at 70° C. After 30 min, the solution was allowed to cool to room temperature. A 4.9 mL(49.5 mmol) amount of 1-bromo-3-chloropropane was added and the reacting mixture was stirred at room temperature for 24 h. The solvent was removed under reduced pressure and 60 mL water added to the residue. The product was extracted with 3x30 mL of dichloromethane. The combined organic fractions were washed with water and dried over sodium sulphate. The solvent was evaporated under reduced pressure. Purification by column chromatography (DCM:MeOH(NH3), 99:1 (v/v)) was performed and enabled to collect the product as an oil.3-(N-Pyrrolidinyl)propanethiol [0373] To a suspension of l-bromoro-3-chloropropane (30.00 g, 191 mmol) and potassium carbonate (17.00 g, 123 mmol) in dichloromethane (160 ml) was added pyrrolidine (3.50 g, 49 mmol) portions. The mixture was stirred at room temperature overnight. Then the mixture was filtered and evaporated under reduced pressure. The residue was purified by chromatography (ethyl acetate/methanol = 95/5) to give 6.00 g of product. [0374] A mixture of l-(3-chloropropyl)pyrrolidine (3.4 g, 23 mmol) and thiourea (1.8 g, 23 mmol) in 95percent ethanol (55 ml) was heated to reflux for 24 hours. A solution of sodium hydroxide (1.20 g, 30 mmol) in water (10 ml) was added, and the mixture was continued to reflux for another 3 hours. After cooled to room temperature, the mixture was evaporated under reduced pressure. The residue was mixed with benzene. The organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 1.80 g of crude product, which was used for the addition reaction.

Molecular Weight:147.64
XLogP3:1.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:147.0814771
Monoisotopic Mass:147.0814771
Topological Polar Surface Area:3.2
Heavy Atom Count:9
Complexity:69.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes