Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Bis(2-bromoethyl) ether | HCID 21521 | — |
| Reactant | HCID 178419079 | HCID 178419079 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178453985 | HCID 178453985 | 70% |
Reaction Steps
To a solution of 21.43 g (0.1 mol) of tert-butyl N-(trans-4-aminocyclohexyl)carbamate in 250 mL of N,N-dimethylformamide were added 16.76 mL (0.12 mol) of bis(2-bromoethyl)ether and 34.85 mL (0.25 mol) of triethylamine, and the mixture was stirred for 6 hours at 70° C. Then solvent was removed under reduced pressure and the residue was treated with ethyl acetate. The organic layer was washed with sodium carbonate aqueous solution and saturated saline solution, then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform alone to chloroform/methanol=30/1) to give 19.92 g (70%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08901315B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-bb8fb3002667436cb2f78bd65119d14e |
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| Source note | uspto-grants-2014_12 |
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