Ethylenediamine → HCID 88095815, compound

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Reaction Steps

A solution of Compound A from Example 1 (10 g, 73.8 mmol) was added dropwise to a stirred solution of 1,2-diaminoethane (25 g, 416.7 mmol) in methanol (10 mL) at 0° C. After the addition was complete, the mixture was left overnight at room temperature with stirring. Removal of the methanol in vacuo gave a light yellow oil which was dissolved in water. The pH of the solution was adjusted to about 11. The solvent was removed under vacuum, and the residue was extracted with ethyl acetate. Evaporation of the organic phase gave a light yellow semi-solid which on crystallization with ether gave the product as a crystalline solid. Yield: 5.89 g (50%); mp. 65°-67° C. 1H NMR (CDCl3) δ1.22[s, 6H, C(CH3)2 ], 1.87[s, 3H, C(=N)CH3 ], 2.49(t, 2H, CH2NH2) and 2.88(m, 2H, NHCH2). MS: (M+H)+ =160.

Provenance & Evidence