Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-([1,1'-Biphenyl]-4-yl)-N-methyl-2-(pyrrolidin-1-yl)ethan-1-amine | HCID 2756716 | — |
| Reactant | N-(3,4-dichlorophenyl)-N-methylglycine | HCID 57418650 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 44561157 | HCID 44561157 | 58.2% |
Reaction Steps
[1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]methylamine (50 mg, 0.18 mmol) was added to a solution of N-(3,4-dichlorophenyl)-N-methylglycine (49 mg, 0.21 mmol), (benzotriazol-1-yloxy) tris(dimethylamino) phosphonium-hexaflurophosphate (BOP) (118 mg, 0.27 mmol) and triethylamine (TEA) (54 mg, 0.54 mmol) in dichloromethane (DCM) (2.0 mL), The reaction mixture was stirred at room temperature for 3 h and was then concentrated in vacuo. To the residue was added 4 mL of saturated solution of Na2CO3 and then extracted by ethyl acetate (2×3 mL). The combined organic layers were concentrated in vacuo to give a brown solid, which was purified by using a Gilson preparative HPLC system (Phenomenex 75×30 mm column, 40 mL/min flow rate, A: 0.1% TFA in acetonitrile B: 0.1% TFA in water, A: 10 to 100% over 15 min, UV detection at 215 nm) to yield the title compound (52 mg, 58%). MS (ES) m/e 496 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07432258B2 |
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| Source dataset | uspto-grants-2008_10 |
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| ORD ID | ord-ffacb749cf924751afffb9b87318792f |
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| Source note | uspto-grants-2008_10 |
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