HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → N'-(tetrahydro-1H-pyrrolizin-7a(5H)-ylmethyl)-2-(2propyloxy)phenylurea
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Phosgene | HCID 6371 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(1-Methylethoxy)benzenamine | HCID 34436 | — |
| Reactant | (Hexahydro-1H-pyrrolizin-7A-YL)methanamine | HCID 10654304 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | N'-(tetrahydro-1H-pyrrolizin-7a(5H)-ylmethyl)-2-(2propyloxy)phenylurea | HCID 15224942 | 85% |
Reaction Steps
2-isopropoxy-aniline (123 mg, 0.813 mmole) was dissolved in CHCl3 (1 ml), added triethyl amine (0.113 ml, 0.813 mmole). Cooled soln. to 0° C., added a solution of phosgene in toluene (0.458 ml, 0.927 mmole) and stirred for 1.5 hours. To this solution was added tetrahydro-1H-pyrrolizin-7a(5H)-methylamine (114 mgs, 0.813 mmole) in CHCl3 and stirred for 18 hours. Solvent removed via rotary evaporator to give crude product as a solid. Solid was chromatographed on silica gel eluting with 5% CH3OH(NH3 ↑)/CHCl3 to give 220 mg (85%) of title compound as free base.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05612366 |
| Source dataset | uspto-grants-1997_03 |
| ORD ID | ord-9055b495843d4c9e9af05f6695e4aa06 |
| Source note | uspto-grants-1997_03 |