반응 #64749

반응 방정식

aniline

1-Methyl-5-(3-Amino-4-Methoxyphenyl)-2-Imidazolidinone

norcamphor

sodium

cyanoborohydride

NaOH

→

product

1-Methyl-5-[3-(Bicyclo[2.2.1]hept-2-ylamino)-4-Methoxyphenyl]-2-Imidazolidinone

용매

ether

ethyl acetate

acetic acid

반응 조건

후처리

1. 1
   workup.ADDITIONThe reaction is poured onto ice
2. 2
   추출The aqueous is extracted with methylene chloride
3. 3
   건조dried over MgSO4
4. 4
   여과filtered
5. 5
   농축concentrated vacuo
6. 6
   기타to afford a brown oil which
7. 7
   농축concentrated in vacuo
8. 8
   기타to yield a white paste which

실험 절차

The aniline of Example 51 (3.07 g, 17.95 mmol) is dissolved in 60 ml of glacial acetic acid and to this is added norcamphor 2.37 g, 21.54 mmol). The reaction is cooled to 5° C. and to it is added sodium, cyanoborohydride (1.36 g, 21.54 mmol). The reaction is poured onto ice and is pH adjusted to 7 with 1 normal NaOH solution. The aqueous is extracted with methylene chloride dried over MgSO4, filtered and concentrated vacuo to afford a brown oil which is flashed on SiO2 with ethyl acetate as the eluent. The appropriate fractions are combined and concentrated in vacuo to yield a white paste which is tritarted with ether to yield (0.57 g 10%) of the product as a white crystalline solid. MP=171°-174° C.

출처