반응 #48551

반응 방정식

1-BOC-piperidine-4-carboxylic acid

4-chloroaniline

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

triethylamine

→

desired compound

tert-Butyl 4-{[(4-chlorophenyl)amino]carbonyl}piperidine-1-carboxylate

용매

acetonitrile

반응 조건

후처리

1. 1
   농축concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
3. 3
   기타partitioned with 2N hydrochloric acid
4. 4
   여과The resulting precipitate was filtered off
5. 5
   workup.DISSOLUTIONre-dissolved in dichloromethane
6. 6
   건조the solution was dried over MgSO4
7. 7
   기타evaporated under reduced pressure
8. 8
   기타The residue was triturated with ether

실험 절차

1-BOC-piperidine-4-carboxylic acid (100 g, 437 mmol), 4-chloroaniline (61.2 g, 480 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (100 g, 524 mmol) and triethylamine (182.6 mL, 1.31 mol) were dissolved in cold (10° C.) acetonitrile (1.75 L). The reaction mixture was stirred for 54 hours at room temperature and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and then partitioned with 2N hydrochloric acid. The resulting precipitate was filtered off, re-dissolved in dichloromethane, the solution was dried over MgSO4 and evaporated under reduced pressure. The residue was triturated with ether to afford the desired compound as a white solid.

출처