Reaction #66221

Reaction equation

potassium carbonate

8-dibenzylamino-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester

Benzyl bromide

(6-amino-1H-indol-3-yl)acetonitrile

sodium iodide

→

(6-dibenzylamino-1H-indol-3-yl)-acetonitrile

Solvents

water

DMF

Conditions

Workup

1. 1
   Otherat ambient temperature
2. 2
   Extractionextracted with ethyl acetate
3. 3
   WashThe combined extracts were washed with ammonium chloride solution
4. 4
   Otherevaporated in vacuo
5. 5
   OtherThe residue was purified by chromatography on silica gel eluting with hexane-ethyl acetate (85:15)

Procedure

To prepare 8-dibenzylamino-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid ethyl ester: Benzyl bromide (10 mL, 84.2 mmol) was added to a stirred mixture of (6-amino-1H-indol-3-yl)acetonitrile (Brown, R. K.; Garrison, R. A., J. Am. Chem. Soc. (1955), Vol. 77, pp. 3839-3842) (5.16 g, 30.14 mmol), potassium carbonate (10.83 g, 78.36 mmol), sodium iodide (560 mg, 3.74 mmol) and anhydrous DMF (150 mL) at ambient temperature under nitrogen. The resulting mixture was stirred at ambient temperature overnight, then poured into a mixture of water, and extracted with ethyl acetate. The combined extracts were washed with ammonium chloride solution, and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with hexane-ethyl acetate (85:15) to give (6-dibenzylamino-1H-indol-3-yl)-acetonitrile (8.8 g); MS (ES): 352 (MH+), which was then treated in a manner similar to that described in Example 34C-G but replacing (6-benzyloxy-1H-indol-3-yl)acetonitrile with (6-dibenzylamino-1H-indo-3-yl)acetonitrile at Step C.

Source