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ChemicalBook CAS DataBase List N-(2-AMINOETHYL) CYCLOPAMINE
334616-31-8

N-(2-AMINOETHYL) CYCLOPAMINE synthesis

1synthesis methods
-

Yield:334616-31-8 88%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran; for 3 h;Heating / reflux;

Steps:



Lithium aluminum hydride (939 μL of a 1M solution in THF, 939 μmoles) was added to a suspension of 16 (110 mg, 235 μmoles) in THF (6 mL). The reaction was refluxed for 3 h and then quenched with water (5 mL) and aqueous KOH (10 mL of a 10% solution). After extracting the mixture with chloroform (2 x 20 mL), the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification by flash chromatography (SiO2, step-wise gradient from 20:1:0.1 to 20:2:0.1 chloroform/methanol/triethylamine) yielded the diamine as a colorless oil (94.4 mg, 208 μmoles, 88%). LRMS: (ES+) calcd for C29H46N2O2 (M + H): 455; found: 455. 1H NMR: spectrum is consistent with the predicted structure.

References:

EP1235851,2006,B1 Location in patent:Page/Page column 47