HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 69829839, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | Methyl 3-(bromomethyl)benzoate | HCID 517981 | — |
| Reactant | Isopropanol hydrochloride | HCID 21912024 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69829839 | HCID 69829839 | 64% |
Reaction Steps
A solution of methyl-3-(bromomethyl)benzoate (7 g, 30.5 mmol) in toluene (170 ml) was heated with pyrrolidine (4.5 g, 64.1 mmol, 2.1 eq.) for at 80° C. for 17 hrs. After addition of Na2CO3, and extraction of the aqueous phase with EtOAc, the organic phase was washed with brine and dried with Na2SO4 Solvent evaporation then afforded the crude product as a yellow oil. This material was dissolved in MeCN and a slight excess of 6N HCl/iPrOH added. After stirring for 30 min. the hydrochloride salt was filtered off and washed with ether to afford the title compound (5 g, 19.5 mmol, 64% yield) as a white solid. MS: m/e=219 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06265426B1 |
| Source dataset | uspto-grants-2001_07 |
| ORD ID | ord-ac3fb33572554dd092fdc9825177bc9a |
| Source note | uspto-grants-2001_07 |