반응 #1183368

반응 방정식

1-(3-chloropropyl)piperidine

1-(3-chloropropyl)piperidine hydrochloride

5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

NaH

→

title compound

수율 90.0%

5-Oxo-4-(3-piperidin-1-yl-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

수율 90.0%

용매

NaOH

toluene

DMA

반응 조건

후처리

1. 1
   추출extracted with toluene (200 ml)
2. 2
   건조The organic phase was dried over Na2SO4]
3. 3
   workup.STIRRINGstirred overnight
4. 4
   workup.WAITAfter 2 h at 50° C.
5. 5
   온도cooling to RT
6. 6
   기타evaporated
7. 7
   workup.DISSOLUTIONdissolved in sat. aq. NaHCO3/Et2O
8. 8
   건조After reextraction with Et2O, the organic phase was dried (Na2SO4)
9. 9
   기타evaporated
10. 10
    기타crystallized from pentane

실험 절차

A solution of 8.52 g (39.75 mmol) of 5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester in 200 ml of DMA was treated at 0° C. with 2.60 g (59.6 mmol) of NaH (55% dispersion in oil) in small portions. The reaction was stirred 1 h at this temperature, then the free 1-(3-chloropropyl)piperidine in 200 ml toluene was dropped in [49.62 g (250.42 mmol, 6.3 eq.) 1-(3-chloropropyl)piperidine hydrochloride were dissolved in 262 ml of 1 M aq. NaOH solution and extracted with toluene (200 ml). The organic phase was dried over Na2SO4]. The reaction was warmed up to RT and stirred overnight. After 2 h at 50° C. and cooling to RT, the reaction was neutralized with water (50 ml), evaporated and then dissolved in sat. aq. NaHCO3/Et2O. After reextraction with Et2O, the organic phase was dried (Na2SO4), evaporated and crystallized from pentane to yield 12.08 g (90%) of the title compound as white crystals. MS: 340.2 (MH+).

출처