1-Bromo-3-chloropropane → 2-(3-Chloropropyl)octahydrocyclopenta[c]pyrrole

To a suspension of octahydrocyclopenta[c]pyrrole hydrochloride (5.00 g, 33.86 mmol) in acetone (150 mL) was added K2CO3 (35.68 g, 101.59 mmol) and 1-chloro-3-bromopropane (10.56 g, 67.72 mmol) in turn. The reaction mixture was heated to reflux for 12 h under N2. The solvent was removed, and the residue was treated with 200 mL of EtOAc. The mixture was washed with water followed by brine. The mixture was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EtOAc) to afford the title compound (3.06 g, 56.63%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 188.7 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.24-1.28 (m, 1H), 1.38-1.40 (m, 2H), 2.06 (m, 1H), 2.46-2.50 (m, 2H), 2.56-2.57 (m, 3H), 2.63-2.68 (m, 2H), 2.70 (d, J=2.24 Hz, 2H), 2.71-2.73 (m, 2H), 3.60 (m, 2H) ppm.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux for 12 h under N2
3. customThe solvent was removed
4. additionthe residue was treated with 200 mL of EtOAc
5. washThe mixture was washed with water
6. dry with materialThe mixture was dried over anhydrous Na2SO4
7. concentrationconcentrated in vacuo
8. customThe residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EtOAc)

ORD record

ord-dd7d1d83674549b4a29bbff04c4ce034

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181277B2