Dichloromethane → 2-Aminoadamantane

The hygroscopic white solid 2-adamantylamine was prepared by dissolving 2-adamantylamine•HCl (Aldrich) in H2O/NaOH, extracting with methylene chloride, drying with MgSO4, filtering, and rotary evaporating. This reagent (500 mg) was dissolved in methylene chloride (20 mL), put on ice, and acetic anhydride (˜5 equiv.) added dropwise. The reaction was left to run overnight, and worked up by addition of sodium bicarbonate solution, and extraction with MeCl2. The solution was washed twice with H2O and dried with MgSO4. The white crystalline product looked clean by TLC (50% CH2Cl2/EtOAc, imaged with paraanisaldehyde, rf˜0.25) and NMR without further purification. 1H NMR (CDCl3): δ 1.62–1.90 (m's, 15H), 4.05 (br's, —CH3), 5.82 (br's, N—H, amide).

1. extractionextracting with methylene chloride
2. dry with materialdrying with MgSO4
3. filtrationfiltering
4. dissolutionThis reagent (500 mg) was dissolved in methylene chloride (20 mL)
5. additionadded dropwise
6. waitThe reaction was left
7. washThe solution was washed twice with H2O
8. dry with materialdried with MgSO4
9. customThe white crystalline product looked clean by TLC (50% CH2Cl2/EtOAc, imaged with paraanisaldehyde, rf˜0.25) and NMR without further purification

ORD record

ord-b59f61164f10402486ac78ace3b3c294

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105310B1