반응 #799616

반응 방정식

octahydrocyclopenta[c]pyrrole hydrochloride

K2CO3

1-chloro-3-bromopropane

→

title compound

수율 56.6%

2-(3-chloropropyl)octahydrocyclopenta[c]pyrrole

수율 56.6%

용매

acetone

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도to reflux for 12 h under N2
3. 3
   기타The solvent was removed
4. 4
   workup.ADDITIONthe residue was treated with 200 mL of EtOAc
5. 5
   세척The mixture was washed with water
6. 6
   건조The mixture was dried over anhydrous Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was chromatographed with a silica gel column (eluting agent: 1:1 (v/v) PE/EtOAc)

실험 절차

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.

출처