4-Amino-5-chloro-2-methoxybenzoic acid → 4-Piperidinylmethyl 4-amino-5-chloro-2-methoxybenzoate

1,1-carbonyldiimidazole (0.8 g., 0.005 mol) was added to a solution of 4-amino-5-chloro-2-methoxy-benzoic acid (1 g, 5 mmol) in THF (20 ml) and the reaction mixture was stirred at room temperature for about 30 minutes. The solvent was evaporated and the residue was taken up in H2O and extracted into ethyl acetate (3×20 ml). The organic phases were collected, dried and evaporated to dryness. The obtained solid residue was dissolved in THF (10 ml) and dropped into a solution of 1-benzylpiperidin-4-yl-methanol [J. Med. Chem. (1992), 35, 4344], (1 g, 5 mmol) in THF (10 ml) and butyllithium (1.6 M in hexane; 3 ml), maintained at 0° C. The reaction mixture was further stirred at room temperature for 1 hour. The solvent was evaporated and the residue was taken up into H2O and extracted into ethyl acetate. The organic extracts were dried and evaporated to give the desired product as a pale yellow oil, (1.63 g).

1. customThe solvent was evaporated
2. extractionextracted into ethyl acetate (3×20 ml)
3. customThe organic phases were collected
4. customdried
5. customevaporated to dryness
6. dissolutionThe obtained solid residue was dissolved in THF (10 ml)
7. temperaturemaintained at 0° C
8. stirringThe reaction mixture was further stirred at room temperature for 1 hour
9. customThe solvent was evaporated
10. extractionextracted into ethyl acetate
11. customThe organic extracts were dried
12. customevaporated

ORD-Eintrag

ord-7fd99fa515d346f1987bde2943c9f9dd

Quelldatensatz

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06002009