N-HYDROXY-ADAMANTANE-1-CARBOXAMIDINE synthesis

Yield:53658-91-6 72%

Reaction Conditions:

with hydroxylamine hydrochloride;sodium hydrogencarbonate in methanol; for 4 h;Reflux;

Steps:

1

46[0100] N-hydroxyadamantanecarboximidamide (46)A suspension of 1-nitrile adamantane (0.96g, 6mmol), hydroxylamine hydrochloride (0.5g, 7.2mmol) and NaHCO₃ (0.6Og, 7.2mmol) in CH30H (15ml) was refluxed for 4hrs, and then concentrated in vacuo to remove CH₃OH. The residue was extracted with ethyl acetate, washed with brine and dried over MgSO4 to afford crude mixture, which was subsequently purified by flash chromatography (5%-15% CH₃OH/CH₂C1₂) to give 46 as white solid (0.84g, Yield: 72%). ¹H-NMR (360 MHz, CD₃OD) δ 2.05 (br s, 4H), 2.01 (br s, 3H), 1.86-1.84 (m, 2H), 1.80-1.74 (m, 6H); ¹³C-NMR (90 MHz, CD₃OD) δ 41.09, 40.87, 37.92, 36.88, 29.88, 28.78; ESI- MS: Calculated for C₁₁H₁₈N₂O (M + H)⁺ 195.3, Found: 195.7. HCI

References:

WO2011/22191,2011,A1 Location in patent:Page/Page column 31