Réaction #64749

Équation de réaction

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

Solvants

ether

ethyl acetate

acetic acid

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONThe reaction is poured onto ice
2. 2
   ExtractionThe aqueous is extracted with methylene chloride
3. 3
   Séchagedried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated vacuo
6. 6
   Autreto afford a brown oil which
7. 7
   Concentrationconcentrated in vacuo
8. 8
   Autreto yield a white paste which

Mode opératoire

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.

Source