Triethylamine → HCID 54552546, Verbindung

Step 1): A solution of SOCl2 (0.5 ml, 6.6 mmol) in chloroform (10 ml) was added dropwise to a solution of 3,5-dimethoxy-2-nitrobenzoic acid [Bull. Soc. Chim. Fr., 127, 258 (1990)] (1.0 g, 4.4 mmol) and a catalytic amount of DMF in chloroform (20 ml) at room temperature. The reaction mixture was refluxed for 1 hour and then concentrated. The residue was dissolved in THF (10 ml). The THF solution was added dropwise to a solution of 4-amino-1-diphenylmethylpiperidine (1.2 g, 4.4 mmol) and triethylamine (0.5 ml, 6.6 mmol) in THF (20 ml) at 5° C. The mixture was stirred at room temperature for 1 hour and then concentrated. The residue was dissolved in ethyl acetate and washed with water. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (10% ethyl acetate in dichloromethane) to give 3,5-dimethoxy-2-nitro-N-(1-diphenylmethylpiperidin-4-yl)benzamide (81.0%): mp 148°-150° C.

1. customat room temperature
2. temperatureThe reaction mixture was refluxed for 1 hour
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in THF (10 ml)
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in ethyl acetate
7. washwashed with water
8. dry with materialThe organic layer was dried (MgSO4)
9. concentrationconcentrated
10. customThe residue was purified by column chromatography on silica gel (10% ethyl acetate in dichloromethane)

ORD-Eintrag

ord-d60adb7ba0df4aa2bbd7511c9155db18

Quelldatensatz

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05872115