1-Butyne, 3-chloro-3-methyl- → 1-(1,1-Dimethyl-2-propyn-1-yl)-4-piperidinol

24 mg cuprous chloride and 15 mg copper powder were added to a mixed solution of 5 ml solution of 7.3 g 4-hydroxypiperidine in diethyl ether (5 ml) and water (2.5 ml) in a nitrogen atmosphere. The mixture was ice-cooled, and 2.5 ml solution of 2.7 ml 3-chloro-3-methyl-1-butyne in diethyl ether was added dropwise thereinto at a bulk temperature of 17 to 22° C. Then, it was stirred at room temperature overnight. Water was added thereto, and the resulting mixture was extracted with diethyl ether for 5 times. The organic layers were combined, and dried over potassium carbonate and then over potassium hydroxide, and filtered. The filtrate was concentrated at normal pressure. The resulting crystalline residues were collected by filtration by adding ethyl acetate/hexane thereto to give 2.54 g of the title compound.

1. temperaturecooled
2. customat a bulk temperature of 17 to 22° C
3. extractionthe resulting mixture was extracted with diethyl ether for 5 times
4. dry with materialdried over potassium carbonate
5. filtrationover potassium hydroxide, and filtered
6. concentrationThe filtrate was concentrated at normal pressure
7. filtrationThe resulting crystalline residues were collected by filtration
8. additionby adding ethyl acetate/hexane

ORD record

ord-581faf23c8854cc699a0ee6dafbf43cc

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06699870B2