Triethylamine → 1-(4-bromophenyl)-N,N-dimethylpiperidin-4-amine

A solution of triethylamine (0.987 mL, 7.08 mmol) in ethanol (6.2 mL) and methanol (4.2 mL) was treated with 1-(4-bromophenyl)piperidin-4-one (0.9 g, 3.54 mmol) and dimethylamine hydrochloride (0.578 g, 7.08 mmol). Titanium(IV) isopropoxide (2.075 mL, 7.08 mmol) was added and a thick mixture formed. The suspension was stirred at ambient temperature for 18 hours. Sodium borohydride (0.2 g, 5.31 mmol) was then added portion-wise over 5 minutes and the reaction mixture was stirred at ambient temperature for 18 hours. The reaction was quenched with 70 mL 10% aqueous ammonia and the resulting suspension was extracted with 250 mL dichloromethane. The aqueous layer was extracted with 150 mL additional dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was purified by flash chromatography on a silica gel column eluting with a gradient of from 0% to 7% methanol in dichloromethane to provide the title compound. MS ESI(+) m/z 284.8 [M+H]+.

1. customa thick mixture formed
2. stirringthe reaction mixture was stirred at ambient temperature for 18 hours
3. customThe reaction was quenched with 70 mL 10% aqueous ammonia
4. extractionthe resulting suspension was extracted with 250 mL dichloromethane
5. extractionThe aqueous layer was extracted with 150 mL additional dichloromethane
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe concentrate was purified by flash chromatography on a silica gel column
11. washeluting with a gradient of from 0% to 7% methanol in dichloromethane

ORD record

ord-9c999c9852474908a17e687beb0316f5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691810B2