Methyl 4-fluorobenzoate → Methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate

Temperature

100 °C

1-Methyl-1,4-diazepane (15.07 g, 132.00 mmol) was added to methyl 4-fluorobenzoate (7.76 mL, 60 mmol) in DMA (150 mL). The resulting solution was stirred at 100° C. for 40 h. The reaction mixture was evaporated and quenched with 2M sodium hydroxide (50 ml). This was extracted with DCM (3×50 ml). The combined organic extracts were washed with saturated brine (50 ml), dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-methyl-1,4-diazepan-1-yl)benzoate (3.59 g, 24.10%) as a tan waxy solid.

1. customThe reaction mixture was evaporated
2. customquenched with 2M sodium hydroxide (50 ml)
3. extractionThis was extracted with DCM (3×50 ml)
4. washThe combined organic extracts were washed with saturated brine (50 ml)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated to dryness
8. customThe crude product was purified by silica column chromatography
9. washeluting with a gradient of 0 to 10% MeOH in DCM
10. customPure fractions were evaporated to dryness

ORD record

ord-71297f6e18f245419f536eb64c14b8be

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737149B2