Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Benzoyl chloride | HCID 7412 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-(3,4-Dichlorophenyl)-2-pyrrolidin-1-ylethanamine | HCID 16791510 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22129662 | HCID 22129662 | 17.4% |
Reaction Steps
2-(3,4-Dichlorophenyl)-2-(pyrrolidin-1-yl)ethylamine (2.46 g), benzoyl chloride (1.34 g) and triethylamine (1.92 g) were stirred in dichloromethane (25 mL) at 23° C., for 48 hours. The reaction was poured into water, and the separated organic layer was dried, and evaporated to a brown oil (2.85 g). Chromatography, with chloroform (1200 mL) and then methanol:chloroform (5:95) as the eluent, gave an oil. Trituration of the oil with diethylether gave a white solid which was dissolved in dichloromethane and treated with hydrochloric acid (g)/diethylether. The solution was evaporated to give the title compound as a white glass (330 mg); mp 129° C. (after resolidifying); MS: m/z=636(M+1); NMR: 1.78 (m,4), 2.54 (m,4), 3.5 (m,2), 4 (m,1), 6.16 (broad s,1), 7.21 (m,1), 7.42 (m,5), 7.62 (m,2): Analysis Calculated: C, 55.22; H, 5.49; N, 6.78; Found: C, 55.21; H, 5.24; N, 6.59.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06147083 |
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| Source dataset | uspto-grants-2000_11 |
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| ORD ID | ord-f69e261d87284bf69c6b2e5d174fd154 |
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| Source note | uspto-grants-2000_11 |
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