反应详情

4-Nitrophenylacetyl chloride, prepared according to the method described in Example 8 using 4-nitrophenylacetic acid (5.4 g, 29.8 mmol), is dissolved in chloroform (15 mL). This solution is refluxed for 9 hours with a solution of (±)-trans-[2-(4-morpholinyl)]cyclohexanol (5.25 g, 28.3 mmol) in chloroform (15 mL) under nitrogen. The solvent is removed in vacuo, and the residue is partitioned between 1M hydrochloric acid (60 mL) and ether (50 mL). The ether layer is separated and the aqueous layer is washed with more ether (2×50 mL), and then basified by the addition of 50% sodium hydroxide solution. This is then extracted with ether (5×60 mL), and the combined ether extracts are washed repeatedly with water to remove any unreacted aminoalcohol. The ether containing the product is then dried over sodium sulfate, and the solvent is removed to leave the crude free ester. The residue is dissolved in ether (20 mL) and treated with HCl in ether to precipitate the salt. It is washed with ether and recrystallised from hot methanol to yield the title compound.

1. customThe solvent is removed in vacuo
2. customthe residue is partitioned between 1M hydrochloric acid (60 mL) and ether (50 mL)
3. customThe ether layer is separated
4. washthe aqueous layer is washed with more ether (2×50 mL)
5. additionbasified by the addition of 50% sodium hydroxide solution
6. extractionThis is then extracted with ether (5×60 mL)
7. washthe combined ether extracts are washed repeatedly with water
8. customto remove any unreacted aminoalcohol
9. dry with materialThe ether containing the product is then dried over sodium sulfate
10. customthe solvent is removed
11. customto leave the crude free ester
12. customto precipitate the salt
13. washIt is washed with ether
14. customrecrystallised from hot methanol