2-Amino-2-methyl-1-propanol → HCID 22418036, compound

Temperature

-5 °C

80 g of 2-amino-2-methyl 1-propanol was dissolved in 350 ml of methylene chloride, and the solution was cooled to -5° C. 4-Chloro-2-methoxybenzoyl chloride was dissolved in 180 ml of methylene chloride and then slowly dropwise added to the cooled solution. After the dropwise addition, the mixture was stirred at room temperature for 2 hr. The reaction mixture was filtered, and the crystal was washed with methylene chloride. Dilute hydrochloric acid was added to the filtrate and then subjected to phase separation to get an organic phase. The organic phase was dried over anhydrous magnesium sulfate and then concentrated. 120 ml of thionyl chloride was slowly dripwise added at room temperature to 106 g of the resultant oleaginous substance. The mixture was stirred for an additional 1 hr and then concentrated. Water was added to the concentrate for dissolution, and an aqueous sodium hydroxide solution was added to the solution to adjust the pH value to 11. Chloroform was added thereto, and the mixture was extracted, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by column chromatography (chloroform). The yield was 62.3 g.

1. additionslowly dropwise added to the cooled solution
2. additionAfter the dropwise addition
3. filtrationThe reaction mixture was filtered
4. washthe crystal was washed with methylene chloride
5. additionDilute hydrochloric acid was added to the filtrate
6. customsubjected to phase separation
7. customto get an organic phase
8. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
9. concentrationconcentrated
10. addition120 ml of thionyl chloride was slowly dripwise added at room temperature to 106 g of the resultant oleaginous substance
11. stirringThe mixture was stirred for an additional 1 hr
12. concentrationconcentrated
13. additionWater was added to the
14. concentrationconcentrate for dissolution
15. additionan aqueous sodium hydroxide solution was added to the solution
16. additionChloroform was added
17. extractionthe mixture was extracted
18. dry with materialdried over anhydrous magnesium sulfate
19. concentrationconcentrated
20. customThe residue was purified by column chromatography (chloroform)

ORD record

ord-f7a51ca81b064b16a85667028d54ace3

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05298518