1-(4-iodobenzoyl)pyrrolidine synthesis
- Product Name:1-(4-iodobenzoyl)pyrrolidine
- CAS Number:168317-99-5
- Molecular formula:C11H12INO
- Molecular Weight:301.12
Yield:168317-99-5 95%
Reaction Conditions:
Stage #1: 4-iodobenzoic acidwith 1,1'-carbonyldiimidazole in dichloromethane at 20; for 0.583333 h;Inert atmosphere;
Stage #2: pyrrolidine in dichloromethane at 20; for 1.25 h;Inert atmosphere;
Steps:
2
A suspension of 4-iodobenzoic acid (8.68 g, 35 mmol) in dichloromethane (120 ml) was treated portionwise over 5 minutes with solid 1,1'-carbonyldiimidazole (5.67 g, 35 mmol) at room temperature with stirring under an atmosphere of argon. This mix was stirred at room temperature for a further 30 minutes. Pyrrolidine (2.49 g, 35 mmol) was then added to the reaction mixture slowly over 15 minutes. The whole mix was then stirred at room temperature under argon for 1 hour. The reaction mix was washed twice with saturated sodium bicarbonate solution (100 ml each), the organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give the title compound as a brown solid (10.05 g, 95%).1H-NMR (400 MHz, CDCl3) δ: 7.75 (2H, m), 7.26 (2H, m), 3.63 (2H, t, J=7 Hz), 3.40 (2H, m, J=7 Hz), 1.96 (2H, m), 1.88 (2H, m); LC/MS Retention time 2.51 mins/(ES+) 302 (M+H, C11H12INO requires 301).
References:
US2010/137276,2010,A1 Location in patent:Page/Page column 16
123-75-1
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