Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | 3-chloro-N-methylpropan-1-amine | HCID 541874 | — |
| Reactant | Diethyl phosphoric acid | HCID 5166299 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86704395 | HCID 86704395 | 81% |
Reaction Steps
0.8 mL of 37% aqueous formaldehyde solution is added to suspension of 3-chloro-N-methylpropan-1-amine (1.4 g or 1.3 mmol) in dioxane (30 mL), the resulting mixture is slightly heated until it becomes a solution. The solution is cooled to room temperature, 1.6 mL of diethyl phosphate is added thereto, stirring at room temperature for 30 min, and then stirring at 90-100° C. for 3 h, the reaction is completed. The solvent is removed under reduced pressure, and the residue is purified by column chromatography (eluent: 1-4% MeOH in DCM) to obtain 2.3 g target compound (yield: 81%). The analytical data of the obtained product are as follows: 1HNMR (400 MHz, CDCl3): δ=4.17-4.10 (m, 4H), 3.74-3.53 (m, 4H), 3.28-3.08 (m, 2H), 2.80 (s, 3H), 2.25-2.09 (m, 2H), 1.29 (t, J=6.8 Hz, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933230B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-816dfa2830ce41c781457563e177f4ed |
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| Source note | uspto-grants-2015_01 |
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