Reaction #44464

Reaction equation

water

ethyl bromoacetate

triethylamine

trans-7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]-diazepin-1-ylamine

→

title compound

Yield 80.0%

Ethyl trans-[(7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]diazepin-1-yl)amino]acetate

Yield 80.0%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   Extractionextracted with ethyl acetate (3×)
3. 3
   WashThe organic layers were washed
4. 4
   DryingAfter drying (MgSO4)
5. 5
   Otherthe solvents were removed under reduced pressure
6. 6
   OtherThe crude product was purified on silica with heptane/ethyl acetate 8:2

Procedure

To a suspension of trans-7-chloro-1,2,3,4,10,14b-hexahydro-10-methyldibenzo[b,f]pyrido[1,2-d][1,4]-diazepin-1-ylamine (100 mg, 0.25 mmol) in DMF (2 mL) was added ethyl bromoacetate (56 μl, 0.51 mmol) and triethylamine (107 ul, 0.76 mmol). The resulting reaction mixture was heated to 60° C. and stirred for 5 h. The mixture was poured into water and extracted with ethyl acetate (3×). The organic layers were washed with sat (aq) NaHCO3 and brine. After drying (MgSO4), the solvents were removed under reduced pressure. The crude product was purified on silica with heptane/ethyl acetate 8:2 to afford 80 mg (80%) of the title compound.

Source