反応 #691574

反応方程式

5-Chlorovaleronitrile

piperidine

potassium carbonate

potassium iodide

lithium aluminium hydride

sodium potassium tartrate

→

5-Piperidinopentylamine

収率 59.0%

溶媒

ethanol

tetrahydrofurane

water

反応条件

後処理

1. 1
   その他The solvent was removed under reduced pressure
2. 2
   抽出extracted with methylene chloride
3. 3
   その他The organic layer was purified by column chromatography on silica gel
4. 4
   workup.ADDITIONwas added dropwise
5. 5
   ろ過The residue was filtered off
6. 6
   その他the filtrate purified by column chromatography on silica gel
7. 7
   その他The residue was crystallized with hydrochloric acid from diethyl ether/2-propanol

実験手順

5-Chlorovaleronitrile (10 mmol), 20 mmol of piperidine, 20 mmol of potassium carbonate and a catalytic amount of potassium iodide in 50 ml of ethanol were refluxed for 6 hours. The solvent was removed under reduced pressure, the residue suspended in water and extracted with methylene chloride. The organic layer was purified by column chromatography on silica gel using methylene chloride/methanol/aqueous ammonia (90/10/1) as eluent (Yield: 59%). The product was added dropwise to a suspension of 25 mmol of lithium aluminium hydride in 25 ml of dry tetrahydrofurane at 0° C. After refluxing for 1 hour 10 ml of a saturated solution of sodium/potassium tartrate in water was added dropwise. The residue was filtered off and the filtrate purified by column chromatography on silica gel using methylene chloride/methanol/aqueous ammonia (90/10/1) as eluent. The residue was crystallized with hydrochloric acid from diethyl ether/2-propanol.

出典