Hydrochloric Acid → HCID 9969778, compound

Participants

Reaction Steps

(Chart D, Step 1): A round bottom flask is charged with 3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (1.17 g, 4.23 mmol) and ethyl ether (21 mL). The yellow homogeneous solution is cooled with an ice bath for 10 minutes. Oxalyl chloride (0.37 mL, 4.23 mmol) is added drop-wise. A yellow precipitate is observed, turning into a gel. After 10 minutes of stirring the ether is removed under reduced pressure. Ethanol (21 mL) is quickly added to the yellow residue and a nitrogen stream is established on the surface of the reaction to remove excess HCl. Using a syringe, triethylamine (1.30 mL, 9.31 mmol) is added dropwise forming HCl gas which is carried away by the nitrogen stream. After the triethylamine addition is complete, the flask is adapted with a reflux condenser, and the reaction is heated to reflux for two hours. The reaction is then cooled and concentrated to 2.79 g of a yellow solid. The crude solid is purified on silica gel using a gradient from 25% to 50% ethyl acetate/heptane as the eluent to give 1.293 grams of ethyl 2-(3-benzyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-2-oxoacetate as a yellow solid. Anal. Calculated for C23H24N2O3: C, 73.38; H, 6.43; N, 7.44. Found; C, 73.02; H, 6.55; N, 7.38.

Provenance & Evidence