Ammonium Chloride → HCID 59830372, compound

Temperature

0 °C

Potassium tert-butylate (2.1 g, 18.8 mmol, dissolved in 20 ml abs. THF) was added within 30 min to a suspension of methyltriphenylphosphonium bromide (7.5 g, 21 mmol) in dry THF (20 ml) under argon at 0° C. The reaction mixture was stirred for 30 min at 0° C. before 1-benzyl-3-methylpiperidin-4-one (3.05 g, 15 mmol, dissolved in abs. THF (20 ml)) was added dropwise within 30 min at 0° C. The reaction mixture was stirred for 30 min at 0° C. and brought to RT within 1 h and stirred for a further 15 h. For working up, the mixture was added to sat. NH4Cl solution (50 ml) and then extracted with EtOAc (3×20 ml). The desired product S was converted into the corresponding hydrochloride by extraction with 2 N HCl solution (20 ml). The organic phase was washed with water (3×20 ml) and the combined aqueous phases were basified with K2CO3. The product S was obtained in the form of a layer of oil and was separated off by reextraction with EtOAc (3×20 ml). After drying of the combined organic phases over Na2SO4 and removal of the solvent, the desired product S was present in a sufficiently pure form (2.50 g, 83%).

1. additionwas added dropwise within 30 min at 0° C
2. waitbrought to RT within 1 h
3. stirringstirred for a further 15 h
4. extractionextracted with EtOAc (3×20 ml)
5. extractionThe desired product S was converted into the corresponding hydrochloride by extraction with 2 N HCl solution (20 ml)
6. washThe organic phase was washed with water (3×20 ml)

ORD record

ord-7a041af5cb4c41a68da7395de3ea7af2

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772307B2