(R)-4-BENZYL-3-CYANOMETHYLMORPHOLINE synthesis
- Product Name:(R)-4-BENZYL-3-CYANOMETHYLMORPHOLINE
- CAS Number:917572-29-3
- Molecular formula:C13H16N2O
- Molecular Weight:216.28
917572-28-2
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Yield:917572-29-3 95%
Reaction Conditions:
with sodium hydroxide;tetra(n-butyl)ammonium hydrogensulfate in dichloromethane;water; for 20 h;Heating / reflux;
Steps:
6.b
(b) (3R)-4-Benzylmorpholine-3-carbonitrile; To a solution of (3￡)-4-benzyl-3-(chloromethyl)morpholine (1.83 g, 8.1 mmol) in methylene chloride (6 mL) was added a mixture of tetrabutylammonium hydro gensulfate (0.14 g, 0.42 mmol), NaOH (0.033 g, 0.83 mmol) and water (6 mL) followed by KCN (0.54 g, 8.3 mmol). The mixture was refluxed for 20 h and then diluted with methylene chloride. The organic phase was washed twice with water and then separated by means of a phase separator column. The solvent was removed by evaporation and the product was purified by chromatography on silica gel (methanol - methylene chloride 0 to 5%). There was obtained 1.66 g (95%) of (3i?)-4-benzylmorpholine-3-carbonitrile. 1H NMR (SOO MHz, CDCl3): 2.4 (m, IH), 2.6 (dd, IH), 2.6-2.7 (m, IH), 2.8 (dd, IH), 2.9 (m, IH), 3.4 (d, IH), 3.7-3.9 (m, 5H), 7.3 (m, IH), 7.4 (m, 4H): m/z 217 (M+l) +.
References:
WO2006/137790,2006,A1 Location in patent:Page/Page column 33
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