Hydrochloric Acid → Benzonitrile, 2-(2-hydroxy-3-((2-(1H-indol-3-yl)-1,1-dimethylethyl)amino)propoxy)-, hydrochloride (1:1)

A solution of 2-[(2,3-epoxy)propoxy]benzonitrile (18.3 g., 0.10 mole) and 2-(3-indolyl)-1,1-dimethylethylamine (15.2 g., 0.08 mole), in 500 ml. of abs. EtOH was stirred at reflux overnight. After concentration of the reaction mixture to approximately 200 ml. and seeding, crude product began to precipitate. The mixture was then cooled and the precipitate separated by filtration to give 24.8 g. of the free base form of the product, white solid, m.p. 120°-123°. The crude solid was dissolved in 400 ml. of boiling MeOH, and the solution was cooled with stirring, as a by-product 1,1'-[[1,1-dimethyl-2-(1H-indol-3yl)ethyl]imino]bis[3-(2-cyanophenoxy)-2-propanol] precipitated. The by-product was collected on a filter and air dried to give 2.2 g., m.p. 180°-187°. The MeOH filtrate was then taken to dryness. The residual solid was dissolved in 200 ml. of i-PrOH and acidified with ethanolic HCl. Seeding followed by 18 hours standing in the cold afforded the product as the crystalline hydrochloride. Filtration of the mixture gave 19.8 g., of solid, m.p. 179°-183°. One recrystallization from abs. EtOH gave 15.5 g. (48%) of white solid, m.p. 185°-187°. TLC on silica gel (9CH2Cl2, 10 MeOH, 1NH4OH) showed a single spot (Rf =0.5, u.v.).

1. temperatureat reflux overnight
2. customto precipitate
3. temperatureThe mixture was then cooled
4. customthe precipitate separated by filtration
5. customto give 24.8 g
6. dissolutionThe crude solid was dissolved in 400 ml
7. customprecipitated
8. customThe by-product was collected on
9. filtrationa filter
10. customair dried
11. customto give 2.2 g
12. dissolutionThe residual solid was dissolved in 200 ml

ORD record

ord-60072d62dca446e7856bcfc06594aca0

Source dataset

uspto-grants-1980_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04234595