反应详情

384 mg (8.0 mmol, 60% in mineral oil) sodium hydride and 500 μl (8.0 mmol) iodomethane were added in turn to a solution of 1.13 g (4.0 mmol) (1-thiazol-2-yl-piperidin-4-yl)-carbamic acid-tert-butyl ester (see example 5a) for synthesis) in MeCN (40 ml). The reaction solution was stirred for 1 h at RT. Subsequently, a further 192 mg (4.0 mmol, 60% in mineral oil) sodium hydride and 250 μl (4.0 mmol) iodomethane were added and stirring took place for a further hour. Subsequently, 25% aq. ammoniac solution (2 ml) were added and concentration took place in vacuo. The residue was extracted with chloroform. The organic solution was washed with water and brine in turn, dried over MgSO4, filtered, and concentrated in vacuo. This residue was dissolved in EtOH (10 ml) and a sat. ethereal HCl soln (20 ml) was added. After 1 h stirring at RT, concentration took place in vacuo. The residue was taken up by ether (20 ml) and water (30 ml) was added. After separation of the organic phase, the aqueous phase was made basic (pH>11) with a 20% NaOH soln. Extraction subsequently took place with chloroform. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. 786 mg (3.99 mmol, 99%) N-methyl-1-(thiazol-2-yl)piperidine-4-amine were thus obtained.

1. stirringstirring
2. concentrationconcentration
3. extractionThe residue was extracted with chloroform
4. washThe organic solution was washed with water and brine in turn
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThis residue was dissolved in EtOH (10 ml)
9. additiona sat. ethereal HCl soln (20 ml) was added
10. stirringAfter 1 h stirring at RT
11. concentrationconcentration
12. additionwas added
13. customAfter separation of the organic phase
14. extractionExtraction subsequently took place with chloroform
15. dry with materialThe organic phase was dried over MgSO4
16. filtrationfiltered
17. concentrationconcentrated in vacuo