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ChemicalBook CAS DataBase List 1,9-BIS-BOC-1,5,9-TRIAZANONANE
82409-02-7

1,9-BIS-BOC-1,5,9-TRIAZANONANE synthesis

12synthesis methods
-

Yield: 86%

Reaction Conditions:

Stage #1:1,1'-carbonyldiimidazole;tert-butyl alcohol in toluene at 60; for 5 h;Inert atmosphere;
Stage #2:bis(3-aminopropyl)amine in toluene at 120; for 18 h;

Steps:

1.1.i di-tert-Butyl (azanediylbis(propane-3,l-diyl))dicarbamate (1):
1 , 1 '-Carbonyldiimidazole (CDI) (13.60 g, 84 mmol) was suspended in a mixture of toluene (100 ml) and i-butanol (11.91 g, 15ml, 161 mmol) under nitrogen atmosphere and was heated to 60 °C for 5 h. A solution of norspermidine (5.77 g, 6.2 ml 44 mmol) in toluene (60 ml) was added dropwise. The reaction mixture was refluxed at 120 °C for 18 h, then cool and concentrated under vacuum. The resulting liquid was extracted in dichloromethane, washed with distilled water and finally dried over anhydrous Na2S04, filtered and concentrated in vacuo to give di-tert- butyl (azanediylbis(propane-3,l-diyl))dicarbamate as a white powder (12 g, 86%). 1H NMR (CDC13): δ 5.22 (brs, 2H, -NHCO), 3.21-3.10 (m, 4H, -CH2NHCO), 2.63-2.60 (m, 4H, - CH2NH), 1.65-1.59 (m,4H, -CH2), 1.40 (s 18 H, C(CH3)3).

References:

VYOME BIOSCIENCES PVT. LTD.;GHOSH, Sumana;SINHA, Mau;BHATTACHARYYA, Anamika;SADHASIVAM, Suresh;GHOSH, Shamik;SAMANTA, Ritwik;TANDON, Nupur WO2018/42367, 2018, A2 Location in patent:Page/Page column 72-73