1,5-Dibromopentane → 1-[2-(4-Fluorophenyl)bicyclo[2.2.1]heptan-2-yl]piperidine

Temperature

50 °C

Anhydrous potassium carbonate (0.94 g, 6.8 mmol) and 1,5-dibromopentane (0.47 ml, 3.4 mmol) were added to a crude base of (±) 2-(4-fluoro-phenyl)-bicyclo[2.2.1]hept-2-ylamine (compound 2; Table 1) (0.70 g, 3.4 mmol) in dry DMF (30 ml). The mixture was heated to 50° C. and incubated for 8 hours. The mixture was then stirred overnight at room temperature and subsequently quenched with water. The resultant mixture was extracted with chloroform (3×20 ml). The chloroform extracts were combined and the chloroform was removed using a rotary evaporator. The remaining residue was extracted with ether (2×25 ml), and the ethereal extract was washed with water (2×20 ml) and dried over anhydrous sodium sulfate. A pale yellow oil was obtained after removing the ether. Purification by TLC with a mobile phase of chloroform and diethyl ether (9:1) resulted in a colorless crystalline compound (0.65 g, 70% yield, m.p. 58-59° C.).

1. customsubsequently quenched with water
2. extractionThe resultant mixture was extracted with chloroform (3×20 ml)
3. customthe chloroform was removed
4. customa rotary evaporator
5. extractionThe remaining residue was extracted with ether (2×25 ml)
6. extractionthe ethereal extract
7. washwas washed with water (2×20 ml)
8. dry with materialdried over anhydrous sodium sulfate
9. customA pale yellow oil was obtained
10. customafter removing the ether
11. customPurification by TLC with a mobile phase of chloroform and diethyl ether (9:1)

ORD record

ord-d5e6d73417884044aabb0a11a0d75f88

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703799B2