Application of 6621-59-6,Some common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
EXAMPLE 4Preparation of (R)-4-trimethylammonio-3-[3-[6-(2-phenylethoxy)hex-l- yl]ureido]butyrate Inner SaltPreparation of the intermediate -^-phenylethoxylhexanitrile[0077] Sodium hydride (60% in oil, 1.38 g, 34.38 mmol) was suspended in N,N- dimethylformamide (45 mL) with ice cooling under N2. 2-Phenylethanol (3.43 mL, 28.65 mmol) was added over approx. 5 minutes. After stirring for a further 30 minutes, 6- bromohexanenitrile (4.56 mL, 34.38 mmol) was introduced dropwise. Following complete addition, the mixture was allowed to come to room temperature and was stirred for 19h. Thereafter it was heated to 500C for 3h, then at room temperature for an additional 18h. Water (200 mL) and ethyl acetate (200 mL) were added. The phases were separated and the aqueous phase extracted further with ethyl acetate (2 x 100 mL). The combined organic phases were dried (MgSO4), filtered and evaporated to give a pale, yellow free flowing oil. Chromatography over SiO2 (isohexane-20% ethyl acetate/isohexane gradient) gave the title compound as a colorless oil (1.55 g, 25%). LCMS: Rt = 3.01 min, m/z = 217.92, 154.67, 145.79. 1H NMR (400 MHz, CDCl3): 7.24-7.1 1 (m, 5H), 3.55 (t, J= 7.07 Hz, 2H), 3.37 (t, J = 6.32 Hz, 2H), 3.35 (t, J= 6.57 Hz, 2H), 2.80 (t, J= 7.07 Hz, 2H), 2.23-2.20 (m, 3H), 1.62- 1.40 (m, 10H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromohexanenitrile, its application will become more common.
Reference:
Patent; DARA BIOSCIENCES, INC.; MIDDLEMISS, David; INGOLD, Kenneth, J.; WO2010/8473; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts