Electric Literature of 4535-90-4, These common heterocyclic compound, 4535-90-4, name is 2-Chloro-N-methylethanamine hydrochloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
EXAMPLE 3 1,1a,6,10b-Tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one O-[ 2-(methylamino)ethyl]oxime SPC12 A dispersion of 1.5 g of 40% sodium hydride in mineral oil (0.025 mole of NaH) was thoroughly washed with hexane. To the sodium hydride, a solution of 2.4 g (0.010 mole) of 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one oxime in 40 ml of dry hexamethylphosphoramide (HMPA) was added. The mixture was stirred at 25 for 1 hr under nitrogen. To the oxime salt was added 1.7 g (0.012 mole) of 2-methylaminoethylchloride hydrochloride and the mixture was stirred at 25 for 16 hrs. The reaction was processed as in Example 1 to give 2.5 g of an oil. Chromatography on 25 g of silica gel with ether as the eluent removed unreacted starting oxime. The crude product was obtained with methanol – 1% triethylamine as eluent. Flash distillation (0.1mu, 180 bath) of the methanol fractions gave 1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-one O-[ 2-(methylamino)ethyl]oxime, MP 100- 101C. NMR spectrum (CDCL3): multiplet at delta6.8-7.5 (8H), triplet (J=6 Hz) at 4.2 (2H), triplet (J=6 Hz) at 2.8 (2H), singlet at 2.4 superimposed on a multiplet at 2.1-2.5 (5H) and a multiplet at 1.3-1.8 (3H). Mass. spec: Calcd. for C19 H20 N2 O: 292.1575; Found: 292.1546.
The synthetic route of 4535-90-4 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; E. I. Du Pont de Nemours & Company; US3960956; (1976); A;,
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