HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1667511Generated: October 30, 2026
1-Pyrrolidineethanamine → N-benzyl-5-ethoxymethyl-2-methyl-N'-(2-pyrrolidin-1-yl-ethyl)-benzene-1,3-diamine
https://huagongshe.com/reaction/1667511
Participants
| Role | Name | HCID | Charge |
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| Reactant | 1-Pyrrolidineethanamine | HCID 1344 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | Benzyl-(3-bromo-5-ethoxymethyl-2-methyl-phenyl)-amine | HCID 67416493 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-benzyl-5-ethoxymethyl-2-methyl-N'-(2-pyrrolidin-1-yl-ethyl)-benzene-1,3-diamine | HCID 67416490 | 58,786.801% |
Reaction Steps
A mixture of benzyl-(3-bromo-5-ethoxymethyl-2-methyl-phenyl)-amine (1.253 g, 3.749 mmol), xantphos (134 mg, 0.232 mmol), 1-(2-aminoethyl)pyrrolidine (0.71 mL, 5.639 mmol), Pd2(dba)3 (10 mg, 0.120 mmol), NaOtBu (658 mg, 6.847 mmol) and anhydrous dioxane (40 mL) was heated to 95° C. for 14 h. The reaction was cooled, filtered through celite, rinsed with EtOAc and concentrated. Chromatography (EtOAc/MeOH) afforded N-benzyl-5-ethoxymethyl-2-methyl-N′-(2-pyrrolidin-1-yl-ethyl)-benzene-1,3-diamine (810 g) as an orange liquid. m/z (M+1) 368.36.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08044041B2 |
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| Source dataset | uspto-grants-2011_10 |
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| ORD ID | ord-016b1de1baf144018cd665299772ed79 |
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| Source note | uspto-grants-2011_10 |
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