Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | N,N-Dimethylaminoethyl chloride hydrochloride | HCID 11636816 | — |
| Reactant | HCID 69197427 | HCID 69197427 | — |
| Product | HCID 59681813 | HCID 59681813 | 4% |
Reaction Steps
To a solution containing 500 mg the product from Step 1 (1.7 mmol) in 10 mL DMF was added 200 mg of NaH (60% dispension in oil, 5.1 mmol). After 2 hours at room temperature, 246 mg of 2-(dimethylamino)ethyl chloride hydrochloride (1.7 mmol) was added, and the reaction mixture was heated to 60° C. for 5 hours. The solvent was evaporated in vacuo to yield a residue which was partitioned between ethyl acetate and brine. The organic phase was dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. Purification of the residue by Gilson reverse-phase HPLC afforded the title compound (24 mg, 4%). MS (ES+) m/e 365 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07348339B2 |
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| Source dataset | uspto-grants-2008_03 |
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| ORD ID | ord-0ed5b5476ae54a32a89347e8a107386d |
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| Source note | uspto-grants-2008_03 |
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