Hydrochloric Acid → HCID 57972811, compound

Temperature

110 °C

To (R)-3-aminovaleric acid hydrochloride (5.0 g), were added 1-bromo-4-trifluoromethylbenzene (10.95 g), copper iodide (1.24 g), potassium carbonate (13.5 g) and dimethylsulfoxide (50 ml), the mixture was stirred under nitrogen atmosphere in a sealed vessel at about 110° C. for 46 hours. The reaction mixture was cooled, water (50 ml) and toluene (50 ml) was added thereto, the pH was adjusted to 3-4 with addition of hydrochloric acid (12.5 mL) and the solution was separated. The aqueous layer was extracted with toluene (50 ml) and the combined organic layer was washed with water (50 ml). 28% ammonia water (50 ml) and water (50 ml) were added to the organic layer and the product was extracted with the aqueous layer. To the aqueous layer were added toluene (50 ml) and hydrochloric acid (30 ml) and the solution was separated. The organic layer was concentrated in vacuo at about 60° C. of the bath temperature, n-heptane (16.3 g) was added to the residue and evaporated twice to give the titled compound as an oily residue. The product was used in the next step without purification.

1. temperatureThe reaction mixture was cooled
2. customthe solution was separated
3. extractionThe aqueous layer was extracted with toluene (50 ml)
4. washthe combined organic layer was washed with water (50 ml)
5. addition28% ammonia water (50 ml) and water (50 ml) were added to the organic layer
6. extractionthe product was extracted with the aqueous layer
7. additionTo the aqueous layer were added toluene (50 ml) and hydrochloric acid (30 ml)
8. customthe solution was separated
9. concentrationThe organic layer was concentrated in vacuo at about 60° C. of the bath temperature, n-heptane (16.3 g)
10. additionwas added to the residue
11. customevaporated twice

ORD record

ord-ae3f904c5c4c4566895ac4116f6eea51

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084611B2