Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Bis(2-bromoethyl) ether | HCID 21521 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 28195587 | HCID 28195587 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69076582 | HCID 69076582 | 70.5% |
Reaction Steps
To a solution of N-(4-bromophenyl)-D-phenylalaninamide (500 mg) in N,N-dimethylformamide (5 mL) were added 1,1′-oxybis(2-bromoethane) (545 mg) and diisopropylethylamine (607 mg) and the mixture was stirred at 50° C. for 6 hours. After being cooled to 5° C., the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford (2R)—N-(4-bromophenyl)-2-morpholin-4-yl-3-phenylpropanamide (430 mg) as a powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08211919B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-f8cd037f34ba4175adb3f6451c16fd83 |
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| Source note | uspto-grants-2012_07 |
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