Hydrochloric Acid → 2-Methyl-1-(pyridin-4-yl)propan-1-amine

Temperature

0 °C

4-Pyridinecarbaldehyde (0.5 mL, 5.25 mmol) in tetrahydrofuran (10 mL) was mixed with lithium hexamethyldisilazide in tetrahydrofuran (1 M, 6.3 mL, 6.3 mmol) and stirred at 0° C. for 4 hours and then stirred with isopropylmagnesium bromide in tetrahydrofuran (0.98 M, 6.3 mL, 6.3 mmol) at room temperature for 16 hours. After completion of the reaction, 1 M aqueous hydrochloric acid was added, and the reaction solution was washed with ethyl acetate. After addition of 1 M aqueous sodium hydroxide, the combined aqueous layer was extracted with chloroform. The resulting organic layer was filtered through celite, and the filtrate was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting crude reaction product containing the desired product was used for the next step.

1. additionwas added
2. washthe reaction solution was washed with ethyl acetate
3. additionAfter addition of 1 M aqueous sodium hydroxide
4. extractionthe combined aqueous layer was extracted with chloroform
5. filtrationThe resulting organic layer was filtered through celite
6. dry with materialthe filtrate was dried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe resulting crude reaction product

ORD record

ord-1a333cd4e2524dd6bb9693d9b04fcfee

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440666B2