Dimethylformamide → HCID 71253084, compound

N,N-dimethylformamide (0.27 mL, 3.47 mmol) was added to a solution of tetrahydropyranyl-4-acetic acid (5.0 g, 34.7 mmol) and thionyl chloride (2.53 mL, 34.7 mmol) in DCM (200 mL) at 0° C. After stirring 1 h at RT the solution was cooled to 0° C. N-Ethyl-N-isopropylpropan-2-amine (15.14 mL, 87 mmol) was added, followed by 4-bromoaniline (5.97 g, 34.7 mmol) in 20 mL DCM were added slowly and the solution was stirred at 0° C. After 1 h the reaction was diluted with saturated ammonium chloride and the organics were removed. Ethyl acetate was added and the layers were separated. The aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material N-(4-bromophenyl)-2-(tetrahydro-2H-pyran-4-yl)acetamide as a tan solid.

1. temperaturewas cooled to 0° C
2. additionwere added slowly
3. stirringthe solution was stirred at 0° C
4. customthe organics were removed
5. additionEthyl acetate was added
6. customthe layers were separated
7. extractionThe aqueous layer was extracted with EtOAc
8. washThe combined organic extracts were washed with water, saturated sodium chloride
9. dry with materialdried over sodium sulfate
10. filtrationThe solution was filtered
11. concentrationconcentrated in vacuo

ORD record

ord-590de39d86794795b778989f6a4ce2b1

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735384B2