Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | HCID 21195964 | HCID 21195964 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 21196049 | HCID 21196049 | 73.4% |
Reaction Steps
A solution of cyclopropylamine (1.10 ml, 15.8 mmol) was added to a solution of 4-(2-fluoro-5-bromobenzyloxy)but-2-ynyl bromide (530 mg, 1.58 mmol) in tetrahydrofuran (8 ml). The cloudy reaction mixture was stirred for about thrity minutes. The reaction mixture was then cooled to 0° C., and held at this temperature for about four hours, at which time no starting material remained, as determined by thin layer chromatography. The reaction mixture was diluted with methylene chloride (50 ml) and washed with 1 M potassium carbonate (10 ml). The organic fraction was dried over sodium sulfate. The solvents were removed in vacuo. The resulting oil was further purified by preparative high performance liquid chromatography, affording 362 mg (73%) of the title intermediate as a clear oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06245761B1 |
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| Source dataset | uspto-grants-2001_06 |
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| ORD ID | ord-2b24ac98f9084eb3b2a6b92cc6271dba |
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| Source note | uspto-grants-2001_06 |
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