G. Sosnovsky—J- Lukszo • Primary Amino Groups in Polyamines
129
3.55 mmol, 25% excess) in ethanol (25 ml). The in-
stantly formed white precipitate was collected by filt-
ration and washed with ethanol (2 x 5 ml) and ethyl
ether (2 x 5 ml). Recrystallization of the crude pro-
duct (0.595 g) from water gave 0.472 g (86%) of
pure 27, m.p. 214—216 °C (dec.).
MS (Cl): m/e = 208 (M++ l, 100% — calculated
for free amine), 190 (M+—17, 40%). —IR (KBr): v =
1230,1296,1391,1460,1482,1664.1707,1721,2840,
3070 c m '1. - 'H NMR (D.O/NaOH): (3 = 2.50 (t.
removal of the solvent on a rotating evaporator at
40 °C/20 torr, the residue was dissolved in water
(50 ml) and acidified with oxalic acid dihydrate
(0.63 g, 5.0 mmol). The white precipitate of 2,3-di-
hydro-1,4-phthalazinedione was colleted by filtration
and washed with hot water (2x10 ml). Concentra-
tion of the combined washings and filtrate on a
rotating evaporator at 60 °C/20 torr gave the crude
28. Crystallization from aqueous methanol afforded
0.485 g (67%) of pure 28, m.p. 182—184 °C (dec.).
Mass spectrum could not be recorded because the
sample did not vaporize.
IR (KBr): v = 1228, 1280, 1385, 1404, 1559, 1637,
1703. 1720, 2150-3050 c m '1. - 'H NMR (D.O): (3 =
2.10-2.82 (m. 14H), 3.20-3.77 ppm (m, 16H). -
13C NMR (D20 ): Ö = 21.78. 23.83, 25.67, 35.01,
36.16, 36.70, 44.64, 45.40, 165.33, 176.43 ppm.
4H), 3.16 (t, 4H), 6.75-7.26 ppm (m. 5H).
-
13C NMR (D20/N a0H ): (3 = 39.41, 40.09. 47.44.
50.65, 127.13, 128.88, 132.21, 133.66, 170.68 ppm.
C15H21N3C V l/2 H 20 (387.34)
Calcd
C 45.45 H 5.60 N 10.50,
Found C 45.54 H 5.52 N 10.60.
Preparation o f N',N',N],NI-tetra(3-aminopropyl)-
C25H46N60 18 (718.68)
glutaryl diamide tetraoxalate (28)
Calcd
C 41.78 H 6.45 N 11.69,
Found C 41.46 H 6.07 N 11.50.
A solution of hydrazine hydrate (100%, 0.210 g,
4.2 mmol) in anhydrous ethanol (3 ml) was added
These studies were conducted pursuant to a con-
tract with the National Foundation for Cancer
rapidly to
a boiling suspension of 25 (0.880 g,
1.0 mmol) in anhydrous ethanol (17 ml). The stirred
reaction mixture was boiled with reflux for 4 h. After Research.
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Unauthenticated
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