Dimethylamine → HCID 178419213, compound

Participants

Reaction Conditions

Reaction Steps

Anhydrous (CH3)2NH (50 g, 1.1 mol) was cooled to 0° C. and poured into the glass pressure vessel containing 1 (14.38 g, 0.1 mol) kept at 0° C. The vessel was assembled and kept at room temperature for 81/2 days with occasional shaking each day. The reaction vessel was then cooled to 0° C. and slowly opened. To this solution was added ca. 8 mL of pentane, and the volatile amines were allowed to evaporate off. The remaining amines and solvent were removed by rotary evaporation. A pale yellow liquid was obtained that had ca. 21% unreacted 1 (by proton NMR). The mixture was taken up in CH2Cl2 and washed once with water. The water washing was repeatedly extracted with CH2Cl2 and the proton NMR spectrum of the CH2Cl2 showed that it contained only the starting amide (1). The CH2Cl2 solution containing the product, uncontaminated by 1 (by proton NMR), was dried over MgSO4 and treated with charcoal. The solvent was then removed by rotary evaportation (and the pale yellow oil (10.1 g (77.7%)) was vacuum distilled: bp 110°-112° C. (0.2 torr); IR (CH2Cl2) 3440 (ν(NH)), 2965 (ν(CH)), 2365 (ν(BH)), 1590 (amide I), 1490 (amide II) cm-1, 1HNMR(CDCl3) δ 1.06 (t, CH3CH2), 2.40 (d, CH3N), 3.18 (m, CH2CH3), 5.80 (br s, amine H), 6.45 (br s, amide H); 11BNMR (CDCl3, BF3Et2O)-11.55 (t, JB-H =88 HZ); 13C NMR (CDCl3) 15.26 (CH3CH2, 32.33 (CH2CH3), 42.91 (CH3N). Anal. Calcd for C3H15BN2O: C, 46.20; H, 11.63; N 21.55. Found: C, 45.94; H, 11.58; N, 21.30.

Provenance & Evidence