Pyridine → HCID 58010950, compound

To a cooled (0° C.) solution of triphosgene (5.0 g, 17 mmol) in 50 ml dichloromethane under a nitrogen atmosphere was added dropwise a solution of tetrahydro-3-furanmethanol (5.4 g, 53 mmol) in 10 ml dichloromethane. Pyridine (4.3 ml, 53 mmol) was added dropwise, and the solution was warmed to room temperature. After 2 hours at room temperature a mixture of triethylamine (7.5 ml, 52 mmol) and N-benzylpiperazine (9.5 ml, 54 mmol) was added dropwise with cooling. The resulting mixture was refluxed for 1 hour. The solution was stirred at room temperature overnight under an nitrogen atmosphere. The mixture was washed with aqueous sodium bicarbonate solution (5%, 2×50 ml), and with a solution of saturated aqueous NaCl (50 ml). The organic layer was dried over sodium sulfate, filtered, and evaporated to dryness. The residue was co-evaporated three times with toluene (50 ml) to yield 4-benzyl-piperazine-1-carboxylic acid tetrahydro-furan-3-ylmethyl ester (13.0 g, 81%) as a brownish oil.

1. additionwas added dropwise
2. temperaturewith cooling
3. temperatureThe resulting mixture was refluxed for 1 hour
4. washThe mixture was washed with aqueous sodium bicarbonate solution (5%, 2×50 ml)
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationfiltered
7. customevaporated to dryness

ORD record

ord-a843cd9ef3af4902889524a248ed0772

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08283354B2