Trifluoroacetic acid → HCID 69420863, compound

To a solution of 1-BOC-2-methyl-4-benzylpiperidine (0.29 g, 1.0 mMol) in 5 mL of dichloromethane was added trifluoroacetic acid (TFA) (0.5 mL). After stirring at rt for 10 h the reaction mixture was evaporated in vacuo and azeotroped twice with dichloromethane and twice with hexane. The residue was dissolved in 5 mL of dichloromethane and diisopropylethylamine (1.6 mL, 10 mMol) was added. In a separate flask a mixture of 5-indolecarboxylic acid (0.19 g, 1.2 mMol) and EDAC (0.23 g, 1.2 mMol) was dissolved in 15 mL of dichloromethane and stirred at rt for 5 min. To this reaction mixture was added the first solution, and the resulting mixture stirred at rt for 20 h. The reaction mixture was poured into water and extracted with ethyl acetate (2×50 mL). The combined organic extract was washed with water and brine. The extract was dried over Na2SO4 and evaporated. The residue was chromatographed on a column of silica gel with 1% MeOH-dichloromethane. Evaporation of the desired fractions gave 0.18 g (54%) of the product as an oil.

1. customwas evaporated in vacuo
2. customazeotroped twice with dichloromethane and twice with hexane
3. dissolutionThe residue was dissolved in 5 mL of dichloromethane
4. stirringstirred at rt for 5 min
5. additionTo this reaction mixture was added the first solution
6. stirringthe resulting mixture stirred at rt for 20 h
7. extractionextracted with ethyl acetate (2×50 mL)
8. extractionThe combined organic extract
9. washwas washed with water and brine
10. dry with materialThe extract was dried over Na2SO4
11. customevaporated
12. customThe residue was chromatographed on a column of silica gel with 1% MeOH-dichloromethane
13. customEvaporation of the desired fractions

ORD record

ord-c9147e4d60374590a7ed98f7cd445b85

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06589954B1