N,N'-Dibenzyl-1,3-propanediamine

General procedure: The diimine (1 equiv.) was dissolved in methanol (50mL), after that NaBH4 (2 equiv.) was added in small portionsto the reaction vessel. The mixture was refluxed for15 min; after cooling, water (70 mL) was added carefully.The aqueous phase was extracted with dichloromethane(3 × 50 mL). The combined organic phases were dried overK2CO3, and the solvent was removed under reduced pressureto yield the product.General procedure: To a solution of 7 (2.0 g, 5.944 mmol) in anhydrous EtOH (40 mL) was added NaBHGeneral procedure: Aldehyde (3 eq dissolved in the same mixture of solvents) was added to a solution of diamine (1 eq) in an anhydrous mixture of DCM:methanol (3:1). The mixture was refluxed overnight, the solvent was evaporated and the crude di-imine was dissolved in an anhydrous mixture of DCM:methanol (1:1). The solution was cooled at 0°C, and sodium borohydride (3 eq) was added portionwise. The reaction was allowed to warm to room temperature and stirred for additional 12h. Excess of sodium borohydride was quenched acidifying with 10percent HCl, with subsequent addition of ammonium hydroxide to reach a basic pH. Phases were separated and the aqueous phase extracted with DCM (3×20mL). Combined organic extracts were dried with sodium sulphate and evaporated. Products were purified by flash chromatography. 4.6.1 Synthesis of N1, N3-dibenzylpropane-1, 3-diamine (1) (0050) Following the general reaction conditions for the disubstituted diamines synthesis, the reaction was worked up and purified to afford 97mg of white solid (isolated yield: 79percent). [00344] Example 43. Preparation of N, N'-dibenzylpropane-1, 3-diamine; [00345] Following the same procedure as for the compound of Example 42, using 1, 3-diamino propane (0.5 mL, 6 mmol), NaTo a solution of benzaldehyde (5 mmol, 0.5094 g)in 50 ml of ethanol an ethanolic solution of 1, 3-diaminopropane (2.5 mmol, 0.1853 g) was added dropwise during 10 min at room temperature. After 2 hourssodium cyanoborohydride (10 mmole, 0.628 g) was added and left overnight. Thenthe solution was evaporated and the residue was taken up with 10 ml of waterand extracted two times with 25 ml of CHThe synthesis of N, N-dibencil-1, 3-diaminepropane was performed using the described method.1 A solution of benzaldehyde (3.18 g, 30 mmol) in CHSynthesis ofN, N'-dibenzylpropane-l, 3-diamine; Benzaldehyde (57.2 g, 0.54 mol) was added to a solution of 1, 3-diaminopropane (20.0 g, 0.27 mol) in methanol (100 ml). The solution was heated to 70

Molecular Weight:254.37
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:254.178298710
Monoisotopic Mass:254.178298710
Topological Polar Surface Area:24.1
Heavy Atom Count:19
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes