Dimethylformamide → HCID 21878472, compound

2-Chloro-6-nitro-benzothiazol (200 mg, 0.93 mmol) was placed in a 15 mL vial equipped with a stribar and septum. The vial was purged with argon and charged with DMF (1.0 mL). Diisopropyl-ethylamine (0.37 mL, 2 eq.) was added resulting in a reddish solution. Amino-4-benzylpiperidine (177 mg, 1 eq.) in DMF (1.0 mL) was added via syringe. The dark solution was then heated to 110° C. for 30 minutes in an aluminum block. The mixture was cooled in an ice bath and diluted with water (10 mL) while stirring vigorously. The compound oiled out. Ethyl acetate (25 mL) was added followed by 2 M NaOH (5 mL) was added and the layers shaken and separated. The aqueous phase was extracted with ethyl acetate (25 mL). The combined organic fractions were washed with brine (2×24 mL), dried over MgSO4, filtered and evaporated to give a brown oil. The oil was purified by chromatography on silica gel (2% 2M ammonia/methanol in CH2Cl2) to give a yellow foam (166 mg, 47%). 1H NMR (CDCl3) δ: 8.50 (d, 1H, J=2.4 Hz), 8.20 (dd, 1H, J=2.4, 8.9 Hz), 7.51 (d, 1H, J=8.9 Hz), 7.32 (m, 5H), 5.63 (d, 1H, J=6 Hz), 3.70 (br s, 1H), 3.55 (s, 2H), 2.89 (m, 2H), 2.28–2.11 (m, 4), 1.73–1.56 (m, 2H).

1. customvial equipped with a stribar and septum
2. customThe vial was purged with argon
3. additioncharged with DMF (1.0 mL)
4. customresulting in a reddish solution
5. temperatureThe mixture was cooled in an ice bath
6. additionwas added
7. stirringthe layers shaken
8. customseparated
9. extractionThe aqueous phase was extracted with ethyl acetate (25 mL)
10. washThe combined organic fractions were washed with brine (2×24 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. customevaporated
14. customto give a brown oil
15. customThe oil was purified by chromatography on silica gel (2% 2M ammonia/methanol in CH2Cl2)

ORD record

ord-d14c4e28d372437eb88adcbf601baab8

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141595B2