| Identification | Back Directory | [Name]
3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)- | [CAS]
76272-36-1 | [Synonyms]
76272-36-1
8-benzyl-8-azabicyclo[3.2.1]octan-1-aMine
8-Benzyl-8-azabycyclo (3.2.1)octan-3-amine
Benzyl-8-azabicyclo[3.2.1]octan-3-exo-amine
exo-3-ami-8-benzyl-8-azabicyclo[3.2.1]octane
8-Benzyl-8-azabicyclo[3.2.1]octan-3-exo-amine
exo-8-Benzyl-8-azabicyclo[3.2.1]octan-3-aMine
8-Benzyl-8-azabicyclo[3.2.1]octane-3-exo-amino
exo-3-amino-8-benzyl-8-azabicyclo[3.2.1]octane
(exo-8-Benzyl-8-azabicyclo[3.2.1]oct-3-yl)aMine
3-AMINO-8-BENZYL-8-AZABICYCLO[3.2.1]OCTANE (3-EXO)-
(1R,3s,5S)-8-benzyl-8-azabicyclo[3.2.1]octan-3-amine
(3-exo-8-(PhenylMethyl)-8-azabicyclo[3.2.1]octan-3-aMine
8-Azabicyclo[3.2.1]octan-3-amine,8-(phenylmethyl)-, (3-exo)-
(3-exo)-8-(Phenylmethyl)-8-azabicyclo [3.2.1]octan- 3-amine Fumarate salt | [Molecular Formula]
C14H20N2 | [MDL Number]
MFCD09753144 | [MOL File]
76272-36-1.mol | [Molecular Weight]
216.326 |
| Chemical Properties | Back Directory | [Boiling point ]
110-115 °C(Press: 0.05 Torr) | [density ]
1.082±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Oil | [pka]
10.23±0.20(Predicted) | [color ]
Clear Light yellow to Beige |
| Hazard Information | Back Directory | [Uses]
Intermediate in the preparation of CCR5 receptor antagonists, antibacterial agents and dopamine antagonists | [Synthesis]
General procedure for the synthesis of exo-8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime from 8-benzyl-8-azabicyclo[3.2.1]octan-3-amine:[105] 8-benzyl-8-azabicyclo[3.2.1]octan-3-one oxime (7.65 g, 33 mmol) was dissolved in 1-pentanol (130 mL) at 120 °C. Sodium metal (7.6 g, 0.33 mol, 10.0 eq.) was added in batches over 2 hours. The mixture was stirred and heated under reflux conditions for 5 hours, then cooled to 5°C. The reaction mixture was slowly acidified with 6 M HCl until the pH reached acidic, and then the aqueous phase was further extracted with 6 M HCl (3 x 100 mL). The aqueous layer was gradually alkalized to pH 10 by addition of 5 M NaOH. the resulting aqueous solution was extracted with EtOAc (3 × 100 mL). The organic extracts were combined, dried with MgSO4, filtered and concentrated in vacuum. The crude product was purified by column chromatography (5-10% MeOH/CH2Cl2) to afford pure exo-8-benzyl-8-azabicyclo[3.2.1]octan-3-amine as a solid (2.60 g, 36%). | [References]
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 11, p. 5020 - 5033
[2] Journal of Heterocyclic Chemistry, 1982, vol. 19, # 3, p. 485 - 488
[3] Patent: WO2008/63600, 2008, A2. Location in patent: Page/Page column 11-12; 26
[4] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 2, p. 133 - 137
[5] Medicinal Chemistry Research, 2018, vol. 27, # 8, p. 1906 - 1928 |
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