Bromocyclopentane → 3-(1-Cyclopentylpiperidin-4-yl)-1-propanol

To a solution of 3-(piperidin-4-yl)-1-propanol (4.7 g, 33 mmol) in acetonitril (100 mL) was added potassium carbonate (25 g, 180 mmol) and cyclopentylbromide (24.5 g, 164 mmol) and the reaction mixture was stirred at reflux temperature overnight. The mixture was allowed to cool, then filtered and the solvent evaporated. The residue was dissolved in ethyl acetate (150 mL) and the organic mixture was dried (MgSO4). The mixture was filtered and the solvent was evaporated. The residue was treated with diethyl ether (100 mL) and the organic phase was decanted and evaporated. This afforded 5.8 g of 3-(1-cyclopentylpiperidin-4-yl)-1-propanol contaminated with probably cyclopentylbromide. 1H NMR (400 MHz, CDCl3) δ 1.2-2.0 (m, 17H), 2.05-2.15 (m, 1H), 2.45 (pent., 1H), 2.95-3.05 (m, 2H), 3.55-3.65 (m, 2H), 4.28-4.36 (m, 2H).

1. temperatureat reflux temperature overnight
2. temperatureto cool
3. filtrationfiltered
4. customthe solvent evaporated
5. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
6. dry with materialthe organic mixture was dried (MgSO4)
7. filtrationThe mixture was filtered
8. customthe solvent was evaporated
9. additionThe residue was treated with diethyl ether (100 mL)
10. customthe organic phase was decanted
11. customevaporated

ORD record

ord-128bcdc006914eeba3cc967659fb16fb

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07332508B2