Реакция #417896

Уравнение реакции

compound 1

1-cyano-cyclobutyl-carboxylic acid methyl ester

ethylenediamine

HCl

→

1-cyano-cyclobutyl carboxylic acid (2-amino-ethyl) amide

Растворители

CH3OH

water

Условия реакции

Обработка

1. 1
   Другоеthe mixture was evaporated
2. 2
   ДругоеThe yellow oil was obtained
3. 3
   ПромывкаThe column was eluted first with H2O
4. 4
   Другоеto remove excess ethylenediamine
5. 5
   workup.ADDITIONThe 0.5-1 N HCl solution containing the product
6. 6
   Другоеwas evaporated to dryness
7. 7
   Другоеyielding 6.37 g (60.47%)

Методика

A solution of compound 1 (8.74 g, 0.063 mol) in CH3OH (50 mL) was added to ethylenediamine (3.77 g, 4.25 mL, 0.63 mol) at room temperature. After 15 h at room temperature, the mixture was evaporated. The yellow oil was obtained and dissolved in 20 mL of distilled water, acidulated with HCl to pH 2 and the solution applied to an AG 50W×8 column cation exchange column (200-400 mesh, H+ form, 100 mL of resin, 3.0 cm column diameter). The column was eluted first with H2O to remove excess ethylenediamine and then with a gradient HCl. The 0.5-1 N HCl solution containing the product was evaporated to dryness, yielding 6.37 g (60.47%). MS (ESI): m/z: 168.08 [M+H]+. Anal. Calcd (Found) for C8H13N3O: C, 57.46 (57.02); H, 7.84 (7.49); N, 25.13 (24.88). 1H NMR (D2O, 400 MHz), δ (ppm): 3.46 (t, J=6.0 Hz, 2H, —NHCH2CH2NH2), 3.07 (t, J=6.0 Hz, 2H, —NHCH2CH2NH2), 2.60-2.50 (m, 4H, —CCH2CH2CH2—), 1.94-2.14 (m, 2H, —CCH2CH2CH2—). 13C NMR (D2O, 400 MHz), δ (ppm): 168.99, 119.95, 41.39, 40.59, 39.38, 31.13, 17.09.

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