tert-butyl N-(4-aminobutyl)carbamate → HCID 85975644, compound

To a solution of the BOC protected diamine 9 (2.10 g, 0.01 mol) in anhydrous acetonitrile (50 mL) was added potassium carbonate (5.14 g) and the suspension was stirred at RT for 10 minutes. A solution of 4-bromobutyronitrile (1.65 g, 0.01 mol) in acetonitrile (25 mL) was added and the resulting mixture stirred at 50° C. for 24 hours. TLC (1:10:89 NH4OH:MeOH:CHCl3) showed that the reaction was 95% complete. The mixture was filtered to remove most of the inorganic salts and the acetonitrile was removed in vacuo to give a solid/oily residue that was purified by flash column chromatography (1:5:94 NH4OH:MeOH:CHCl3) to yield the product 10 as a clear oil (1.74 g, 61%), Rf=0.5 (1:10:89 NH4OH:MeOH:CHCl3); 1H NMR (CDCl3) d 4.79 (br s, 1H, NHCO), 3.12 (q, 2H, CH2), 2.74 (t, 2H, CH2), 2.60 (t, 2H, CH2), 2.46 (t, 2H, CH2), 1.81 (quin, 2H, CH2) 1.57-1.37 (m, 13H, 2×CH2, 3×CH3).

1. stirringthe resulting mixture stirred at 50° C. for 24 hours
2. filtrationThe mixture was filtered
3. customto remove most of the inorganic salts
4. customthe acetonitrile was removed in vacuo
5. customto give a solid/oily residue that
6. customwas purified by flash column chromatography (1:5:94 NH4OH:MeOH:CHCl3)

ORD record

ord-316cb1aee89b402c84d11f5313472cc2

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07910363B1