반응 #742697

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

sodium hydroxide

toluene

N,N-dimethylacetamide

반응 조건

후처리

1. 1
   추출extracted with toluene (200 ml)
2. 2
   건조The organic phase was dried over Na2SO4]
3. 3
   workup.STIRRINGstirred over night
4. 4
   workup.WAITAfter 2 h at 50° C.
5. 5
   온도cooling to room temperature
6. 6
   기타evaporated
7. 7
   workup.DISSOLUTIONdissolved in sat. aq. sodium hydrogencarbonate solution/diethyl ether
8. 8
   건조After reextraction with diethyl ether, 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 N,N-dimethylacetamide was treated at 0° C. with 2.60 g (59.62 mmol) of NaH (55% 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 [49.6 g (250 mmol, 6.3 eq.) 1-(3-chloropropyl)piperidine hydrochloride were dissolved in 262 ml of 1 M aq. sodium hydroxide solution and extracted with toluene (200 ml). The organic phase was dried over Na2SO4]. The reaction was warmed up to room temperature and stirred over night. After 2 h at 50° C. and cooling to room temperature, the reaction was neutralized with water (50 ml), evaporated and then dissolved in sat. aq. sodium hydrogencarbonate solution/diethyl ether. After reextraction with diethyl ether, 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