Reacción #977804

Ecuación de reacción

2-[4-(tert-butoxycarbonylamino)-2,3,5,6-tetramethylanilino]acetic acid

1-benzyl-4-aminopiperidine

triethylamine

sodium hydrogen carbonate

→

2-[4-(tert-butoxycarbonylamino)-2,3,5,6-tetramethylanilino]-N-(1-benzyl-4-piperidinyl)acetamide

Rendimiento 73.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with methylene chloride
2. 2
   LavadoThe extract was washed with brine
3. 3
   Otrodried
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   Otroto give a residue
6. 6
   OtroThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1)

Procedimiento

A mixture solution of 2.2 g of 2-[4-(tert-butoxycarbonylamino)-2,3,5,6-tetramethylanilino]acetic acid, 1.67 ml of 1-benzyl-4-aminopiperidine, 10.47 g of 25% propane-phosphonic acid anhydride and 4.76 ml of triethylamine in 40 ml of methylene chloride was stirred over night at room temperature. Then, 20 ml of saturated sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with methylene chloride. The extract was washed with brine, dried and concentrated under reduced pressure to give a residue. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1) to give 2.48 g (73%) of 2-[4-(tert-butoxycarbonylamino)-2,3,5,6-tetramethylanilino]-N-(1-benzyl-4-piperidinyl)acetamide. Then, a mixture of 438 mg of the compound obtained and 40 mg of 20%-palladium hydroxide on carbon in 4 ml of methanol was stirred for 6 hours under 5 atm of hydrogen. Then, the catalyst was filtered off a Celite (trade name) pud and the filtrate was concentrated under reduced pressure to give a residue. The obtained residue was purified by amine-coated silica gel (Fuji Silysia Chemical Ltd.; NH-DM1020) column chromatography (methylene chloride:methanol=10:1) to give 293 mg (81%) of the above-mentioned compound (21).

Fuente