Sodium Carbonate → N-[(1-n butyl-4-piperidyl)methyl] 2-(4-chlorobutoxy)indole-3-carboxamide

A stirred suspension of N-[(1-n butyl-4-piperidyl)methyl] indole-3-carboxamide (Description 1b, 1.0 g, 0.0032 mole) in chloroform (25 ml) was treated with 4-chlorobutanol (0.69 ml, 0.0064 mole) followed by N-chlorosuccinimide (470 mg, 0.0035 mole) and a yellow solution was produced inside 5 minutes. After a further 40 minutes the solution was observed to darken in colour to orange. The mixture was kept at room temperature for a further 1 h then treated with 10% Na2CO3 solution (30 ml) and extracted with chloroform (2×30 ml). The combined extracts were dried (Na2SO4) and concentrated in vazcuo to afford an orange oil, which was chromatographed on silica gel eluting with 5% methanol/chloroform to give N-[(1-n butyl-4-piperidyl)methyl]2-(4-chlorobutoxy)indole-3-carboxamide (0.67 g, 50%) as a yellow oil.

1. customa yellow solution was produced inside 5 minutes
2. waitThe mixture was kept at room temperature for a further 1 h
3. extractionextracted with chloroform (2×30 ml)
4. dry with materialThe combined extracts were dried (Na2SO4)
5. concentrationconcentrated in vazcuo
6. customto afford an orange oil, which
7. customwas chromatographed on silica gel eluting with 5% methanol/chloroform

ORD-Eintrag

ord-d6cc8ebbd451454d8bb6eab2b0904a47

Quelldatensatz

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05998409