Crystal structure of 2,2-diphenyl-4-dimethylaminopentanenitrile, C19H22N2

A. Amani, G. Rezanejade Bardajee, F. Jafarpour, M. O. Razaghi, M. Yousefl Behzadi, A. Haeri
2005 Zeitschrift für Kristallographie - New Crystal Structures  
C 19 H 22 N 2 ,monoclinic, C 1 c 1(no. 9), a =8.636(1) Å, b =15.162(2) Å, c =12.807(2) Å, =106.599(3)°, V =1607.1 Å 3 , Z =4, R gt (F) =0.044, wR ref (F 2 ) =0.088, T =120 K. Source of material The title compound was synthesized by reaction of 1-dimethylamino-2-chloropropane hydrochloride and diphenylacetonitrile in the presence of NaOH as abase. 1-dimethylamino-2-chloro-propane was obtained from the reaction of thionyl chloride and 1dimethylamino-2-propanol whose preparation was described
more » ... was described previously [1] . In atypical procedure, a50%w / v solution of sodium hydroxide in water (12.5 ml, 0.32 mol) was added to amechanically stirred suspension of diphenylacetonitrile (15.0 g, 0.08 mol) and dibenzo-18-crown-6 (0.5 g, cat.) in dimethylsulfoxide (12.5 ml). The color rapidly deepened to an orange/brown. 1-Dimethylamino-2-chloropropane hydrochloride (15 g, 0.095 mol) was added in portions over 30 min, this caused the temperature to rise to 30°C. After the addition was completed the mixture was warmed to 45-50°C (water bath) and stirred for one hour. The reaction mixture was then allowed to cool to room temperature, poured into ice/water (250 ml) and extracted with ethyl acetate (3 ×150 ml). The combined extracts were dried (MgSO 4 ), filtered and evaporated down to 100 ml. The product was extracted into 1NHCl (100 ml +50ml) and then again washed with ethyl acetate. The aqueous solution was basified with 2Msodium hydroxide and extracted into ethyl acetate (3 ×1 00 ml). The extracts were washed with saturated NaCl solution (70 ml), dried (MgSO 4 ), and evaporated down to ayellow oil. This was chilled and titrated with cold hexane (50 ml) to give the title compound (yield 39 %). Recrystallization from hexane gave crystals suitable for X-ray analysis (m.p. 91-92°C). Z. Kristallogr. NCS 220 (2005) 549-550 549
doi:10.1524/ncrs.2005.220.14.579 fatcat:f2qii246bjgu5i4vx52vd4bdou