Dimethylformamide → HCID 22890651, compound

To a solution of the product from Example 156B (0.35 g, 0.838 mmol) in N,N-dimethylformamide (3.0 mL) was added piperidine (0.17 mL, 1.72 mmol), and this mixture was stirred at room temperature for 1 hour. The reaction mixture was partitioned between dichloromethane and water. The isolated organic layer was washed with brine and dried over MgSO4, filtered and evaporated. The residue dissolved in water (1.0 mL) and concentrated sulfuric acid (0.10 mL) was added at room temperature, followed by heating to 50° C. A solution of sodium nitrite (0.25 g) in water (0.60 mL) was added dropwise at 50° C. and the reaction was stirred for 1 hour. The reaction was extracted with ethyl acetate and washed with water and brine. The organic was dried over MgSO4, filtered and evaporated to give the crude product (0.041 g, 25% yield), which was used without further purification.

1. customThe reaction mixture was partitioned between dichloromethane and water
2. washThe isolated organic layer was washed with brine
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated
6. dissolutionThe residue dissolved in water (1.0 mL)
7. additionconcentrated sulfuric acid (0.10 mL) was added at room temperature
8. temperatureby heating to 50° C
9. additionA solution of sodium nitrite (0.25 g) in water (0.60 mL) was added dropwise at 50° C.
10. stirringthe reaction was stirred for 1 hour
11. extractionThe reaction was extracted with ethyl acetate
12. washwashed with water and brine
13. dry with materialThe organic was dried over MgSO4
14. filtrationfiltered
15. customevaporated

ORD record

ord-f1229f4721b14b0686af7ea2f5ee6b6d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834043B2