Isopropanol → HCID 51347808, compound

A mixture of 4-(dimethylammonio)butanoate (4) (7.87 g, 0.06 mol) and ethyl bromide (13.08 g, 0.12 mol) in anhydrous acetone (20 ml) was refluxed until the starting material 4-(dimethylammonio)butanoate disappeared (TLC control, methanol-aquous ammonium hydroxide, 3:1)). The reaction mixture was supplemented with isopropanol (100 ml) and the solution was evaporated to dryness. A solution of solution of KOH (7.28 g, 0.13 mol) in 96% ethanol (70 ml) was added to the residue at 0° C. and reaction mixture was stirred for 4 hours. The precipitate was filtered off and the filtrate was treated with 2 N HCI in methanol until the pH of the medium was 7-8. The reaction mixture was kept at −18° C. for 12 hours and was filtered. The filtrate was evaporated to dryness and the residue was azeotropically dried with isopropanol (3×100 ml). The obtained oily solid (13.4 g) was dissolved in isopropanol (100 ml) and was kept at −18° C. for 12 hours. The precipitate was filtered and the filtrate was evaporated to dryness and crystallized from acetone (30 ml) at −18° C. to give 4.14 g (43%) of 4-[ethyl(dimethyl)ammonio]butanoate.

1. customthe solution was evaporated to dryness
2. customreaction mixture
3. filtrationThe precipitate was filtered off
4. additionthe filtrate was treated with 2 N HCI in methanol until the pH of the medium
5. waitThe reaction mixture was kept at −18° C. for 12 hours
6. filtrationwas filtered
7. customThe filtrate was evaporated to dryness
8. dry with materialthe residue was azeotropically dried with isopropanol (3×100 ml)
9. dissolutionThe obtained oily solid (13.4 g) was dissolved in isopropanol (100 ml)
10. waitwas kept at −18° C. for 12 hours
11. filtrationThe precipitate was filtered
12. customthe filtrate was evaporated to dryness
13. customcrystallized from acetone (30 ml) at −18° C.

ORD record

ord-f0f7475dbbfd458fa52ec1ec5efa5f15

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278907B2