反应详情

To a mixture of 2-[4-(benzoxazol-2-yl)benzyloxy)]ethylamine hydrochloride (0.11 g; 0.38 mmol) dissolved in MeOH (2 ml) and Et3N (0.053 ml; 0.38 mmol) is added dried and powdered 3 Å molecular sieves along with 2-phenylethoxyacetaldehyde (0.11 g; 0.68 mmol). After 1 hour, a 1M THF solution of sodium cyanoborohydride (0.75 ml; 0.75 mmol)is added dropwise. After 2 hours, the reaction mixture is quenched with acetone and 2N HCl and then concentrated in vacuo to dryness. The residue is dissolved in 3 ml 15% 15 NaOH, extracted with Et2O 4x, dried (MgSO4) and concentrated in vacuo to dryness. The residue is purified by column chromatography using 10% MeOH/CH2Cl2. The product is dissolved in EtOH acidified with HCl/EtOH and concentrated to yield N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-2-(2-phenylethoxy)ethanamine hydrochloride as a white solid. (m.p. 174°- 175° C.).

1. customdried
2. waitAfter 2 hours
3. customthe reaction mixture is quenched with acetone and 2N HCl
4. concentrationconcentrated in vacuo to dryness
5. dissolutionThe residue is dissolved in 3 ml 15% 15 NaOH
6. extractionextracted with Et2O 4x
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo to dryness
9. customThe residue is purified by column chromatography
10. dissolutionThe product is dissolved in EtOH
11. concentrationconcentrated