反応 #80847

反応方程式

benzaldehyde

hydrochloric acid

cyclohexylmethyl bromide

2-(aminomethyl)pyridine

sodium hydroxide

→

1-(R,S)-(2-pyridyl)-2-cyclohexylethylamine

収率 43.5%

溶媒

butylmethyl ether

water

反応条件

後処理

1. 1
   workup.STIRRINGAfter stirring for 2-4 hours
2. 2
   workup.STIRRINGThe suspension was stirred for 2 hrs
3. 3
   温度The reaction mixture was refluxed for 36-48 hrs
4. 4
   温度After cooling the mixture, it
5. 5
   workup.STIRRINGstirred for 2-6 hours
6. 6
   その他The organic phase was separated
7. 7
   洗浄The aqueous phase was washed four times with 3 L of methylene chloride
8. 8
   抽出The racemic amine was extracted three times with 4 L of methylene chloride
9. 9
   乾燥dried over sodium sulfate
10. 10
    濃縮concentrated to dryness
11. 11
    workup.STIRRINGThe oil product was stirred with 2 L of hexane
12. 12
    ろ過filtered
13. 13
    濃縮concentrated

実験手順

Under a nitrogen atmosphere, 1.365 kg (12.86 moles) of benzaldehyde was added with stirring and cooling to 1.39 kg (12.86 moles) of 2-(aminomethyl)pyridine maintaining the temperature <50° C. After stirring for 2-4 hours, the mixture was diluted with 13 L oft-butylmethyl ether (MTBE). To the clear solution was added 1.05 kg (27.72 moles) sodium hydroxide (flakes) and 2.375 kg (6.43 moles) of tetrabutylammonium iodide. The suspension was stirred for 2 hrs., then 2.3 kg (12.86 moles) of cyclohexylmethyl bromide was added. The reaction mixture was refluxed for 36-48 hrs. After cooling the mixture, it was diluted with 3 L of water followed by 12 L of 3N hydrochloric acid and stirred for 2-6 hours. The organic phase was separated and discarded. The aqueous phase was washed four times with 3 L of methylene chloride, then basified with 2.5 L of 0.5N ammonium hydroxide solution. The racemic amine was extracted three times with 4 L of methylene chloride, dried over sodium sulfate and concentrated to dryness. The oil product was stirred with 2 L of hexane, filtered and concentrated to yield 1.14 kg (43.5%) of 1-(R,S)-(2-pyridyl)-2-cyclohexylethylamine.

出典